Category: alcohols-buliding-blocks

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 4740-78-7, name is 1,3-Dioxan-5-ol. This compound has unique chemical properties. The synthetic route is as follows. category: alcohols-buliding-blocks

[00768] To a solution of compound 263-1 (2 g, 6.55 mmol, 1 eq) in THF (2 mL) were added compound 263-la (1.02 g, 9.83 mmol, 1.5 eq) and PPh3 (2.58 g, 9.83 mmol, 1.5 eq). The mixture was degassed with N2 for 3 times. Then DIAD (1.99 g, 9.83 mmol, 1.9 mL, 1.5 eq) was added to the mixture dropwised at 0C. The mixture was stirred at 20C for 16 hr. LCMS showed that the starting material was remained and 33% of desired product was detected. TLC (PE/EA = 3/1, UV) showed that several spots were formed. The reaction mixture was concentrated in vacuum and the residue was diluted with EA (20 mL), washed with water (5 mL) and brine (5 mL). The organic phase was dried over Na2S04, filtered and concentrated in vacuum. The crude product was purified by column chromatography (Si02). Compound 263 (1.3 g, 2.79 mmol, 42.6% yield) was obtained. LCMS (ESI): RT = 0.885 min, mass calcd. For Ci8Hi6F3N502,391.13 m/z found 392.0 [M+H] +; 1HNMR (400 MHz, CDC13) 9.02 (s, 1H), 8.20 (dd, J= 7.92, 1.38 Hz, 1H), 7.51- 7.58 (m, 3H), 7.35- 7.42 (m, 1H), 7.30 (d, J= 8.54 Hz, 2H), 7.03- 7.08 (m, 1H), 5.12 (s, 1H), 4.85- 4.94 (m, 2H), 4.65- 4.80 (m, 2H), 4.00 – 4.07 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 4740-78-7.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 56456-49-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 56456-49-6, name is 4-Chloro-2-fluorobenzyl alcohol, molecular formula is C7H6ClFO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(2) Then, 16.5 g of 4-chloro-2-fluorobenzylalcohol was dissolved in 150 ml of tetrahydrofuran and 1 ml of pyridine, to which 10 ml of thionyl chloride was added dropwise at 5 C., and the mixture was stirred for 2.5/6 hours. After cormpletion of the reaction, the reaction mixture was concentrated, and the precipitated crystals were collected by filtration. The filtrate was subjected to silica gel column chromatography, which afforded 18.5 g of 4-chloro-2-fluorobenzyl chloride. 1 H–NMR (250 MHz, CDCl3): delta (ppm) 4.59 (2 H, s), 7.09-7.17 (2 H, m), 7.36 (1 H, dd, J=7.9, 7.9 Hz)

According to the analysis of related databases, 56456-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Ltd.; US6100257; (2000); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1450754-41-2, name is 2-(3-But-3-ynyl-3H-diazirin-3-yl)-ethanol. A new synthetic method of this compound is introduced below., Computed Properties of C7H10N2O

To a solution of ethan1-ol (200 mg,145 mrnoi, 1 equiv) in tetrahydrofuran (10 mL) at 24 C, was added carbonyidiimidazole(950 mg, 580 mmol, 4.00 equiv). The mixture was allowed to stir for 12 hours at 24 eQ Theproduct mixture was concentrated in vacuo to a solid residue. The residue was directly loadedto a hexaneequilibrated silica gel column and the desired material was eluted using a 50–100% ethyl acetate-hexane solvent, two steps). The irnidazole 5 was isolated as colorless oilafter concentration of the residual soR nt (320 mRf= 0.15 (40 ethyl acetate—he?ane; LV). f- NMR (500 MHz, ()Cl.). 8.13 (s, I]1 7.42-7..-1 I ,m, IH, H-. 7.03—7.u2 ,ni. I H 4.26—4 23 a. 2Ff, 7 1 :-iz, F).L99–i.96(m.3RHR:). I H–I S8(t,2H.i==Hz.H). I 6(– I 6{t,2H.i==7.I Hz.H). ?( >R (125 MHz. CDCI ). d I?4X.3 (C). I 7. I (CH. 130 7 Ci). 117. 1 ( H), 82 3(( , 6 (( H). o2 ) {OCH). 32 QH , 32.1) (( RI, 26.0 (CN , I . I ((?Ri) IR (AE R-FTIR) cm? 3291 (brj, 3 1 8 (w) 3 132 (rn,j, 2960 (w), 2921 (m,j, 2858 (m) 1 758 (s), 1588(s). 1525 mL 1473 (m). 1444 (m), 1404 (in), 1350 (w), 1316 (w). 1282 (? . 1240 (w), 1173(w), 1095 (m), 1058 (m) 1003 (v, 898 (m), 833 , 768 (w), 749 ( 6-l (v, 598 (w),526 (w). HRMSESI (m/z) [. L calculated for C H 1N4O2, 233. 1039. Ibund. 233.1064.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1450754-41-2, 2-(3-But-3-ynyl-3H-diazirin-3-yl)-ethanol.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; WOO, Christina, M.; GAO, Jinxu; (555 pag.)WO2018/226828; (2018); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 702-82-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.702-82-9, name is 3-Aminoadamantan-1-ol, molecular formula is C10H17NO, molecular weight is 167.2481, as common compound, the synthetic route is as follows.

Example 8.2: (S)-l-[2-(3-Hydroxy-adamantan-l-ylamino)-acetyl]-pyrrolidine 2- carboxylic acid methyl ester (0115) In a clean and dry 1L four neck R.B.F. equipped with mechanical stirrer, thermometer pocket and a reflux water condenser under nitrogen charged dichloromethane (140 mL, 4V), 3-amino-adamantan-l -ol (35.58 g, 1.25 eq.), powdered potassium carbonate (70.51 g, 3.0 eq.) and potassium iodide (2.82 g, 0.1 eq.) under N2 and Stirred for 30 min. Meanwhile prepared a solution of (S)-l-(2-chloro-acetyl)-pyrrolidine-2-carboxylic acid methyl ester (35 g, l .O eq.) and dichloromethane (35 mL, IV) and added to the reaction mass in one lot. Heated the reaction mass to vigorous reflux and maintained for 6 h. Monitored progress of reaction by HPLC after 4 h. After complete conversion on HPLC, stopped heating and cooled reaction mass to 20-25C. Filtered the salt and washed the solid with DCM (70 mL, 2V). Charged the filtrate in 1 L RBF and cooled reaction mass to 10-15C. A solution of aq. acetic acid (30.2 mL, 3.1 eq.) in water (175 mL, 5 V) was added to above reaction mass. The reaction mass was stirred for 30 min. at 20-25C. The organic layer and aq. Layer were separated. The organic layer was kept aside. The aqueous layer was extracted with dichloromethane (70 mL x 4, 2V x 4). [Collectively organic layers were concentrated to get a compound of formula (16) wherein the Rl is specifically methyl]. After dichloromethane wash, adjusted the pH of aqueous layer using aq. ammonia (3V). The aqueous layer was extracted with dichloromethane (70 mL chi 4, 2V chi 4). All the DCM layers were pooled to gather and washed with brine. DCM was removed under reduced pressure at 60C and 50 torr. Added methanol (70 mL, 2V) to reaction mass and refluxed for 1 h and cooled to 35-40C. Distilled methanol under reduced pressure to displace DCM till the temperature reached at 60C at 50 torr the distillation was stopped and continued heating for 1 h. Added methanol (35 mL, IV) to reaction mass and refluxed for 1 h to prepare homogeneous reaction mass. Cooled reaction mass to 20-25C and unload the methanolic solution of product. Yield range: 80-90 %; HPLC purity > 99.00 %; chiral HPLC purity: 100 %,

Statistics shows that 702-82-9 is playing an increasingly important role. we look forward to future research findings about 3-Aminoadamantan-1-ol.

Reference:
Patent; HIKAL LIMITED; MOHILE, Swapnil Surendra; TAPKIR, Sandeep Rameshrao; PATIL, Manoj Vinayak; GANGOPADHYAY, Ashok Kumar; NIGHTINGALE, Peter David; WO2015/128718; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 57772-50-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 57772-50-6 as follows.

Example 4: An aromatic amino alcohol of formula II (R1 = R2 = R4 = R5 = hydrogen, R3 = 3-methyl, 13.48 g, 98 mmol) was dissolved in a THF/diethoxymethane mixture (1 :1, v:v) (73 g) and charged with water (93 g). The agitated brown mixture was cooled to about 12 C. A parallel dosage of gaseous phosgene (13.7 g, 139 mmol) and 25% aqueous NaOH (62.9 g, 393 mmol) was performed within 1 h wherein the pH was kept between 8 and 9 and the temperature in the reaction vessel was kept at 7 to 17 0C. At the end of the phosgene addition the reaction mixture was additionally agitated for 1 h at 12 C. After workup procedure according to example 1 and drying 100% of compound of formula I (R1 = R2 = R3 = R4 = R5 = hydrogen, 16.19 g) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57772-50-6, its application will become more common.

Reference:
Patent; LONZA LTD; GRIFFITHS, Gareth-John; LORENZI, Miriam; WARM, Aleksander; WO2010/115640; (2010); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 6850-65-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6850-65-3, name is 4-Aminocyclohexan-1-ol(isomers mixture), molecular formula is C6H13NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 4-aminocyclohexanol (23 g,0.2 mol) and Et3N (60 g, 0.6 mol) in THF (230 mL) was added (Boc)20 (87 g, 0.4 mol). The resulting solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with water (2 x 200 mL) and brine (200 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel using DCMI MeOH (V:V, 20:1) to afford the desired product as a white solid. MS: 216.2 (M+1).

According to the analysis of related databases, 6850-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10626; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 4704-94-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4704-94-3 as follows.

(10a) 1,5,9-trioxaspiro[5.5]undec-3-ylmethanol A mixture of 2-(hydroxymethyl)-1,3-propanediol (3.3 g, 31.1 mmol), tetrahydro-4H-pyran-4-one (3.12 g, 31.2 mmol), p-toluenesulfonic acid monohydrate (268 mg, 1.41 mmol) and benzene (68.3 ml) was refluxed in a round bottom flask equipped with a cooling tube and Dean-Stark for 6 hours. After cooled to room temperature, triethylamine (1 ml) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: heptane, heptane/ethyl acetate=1/1, 1/3) to obtain the title compound (3.80 g, yield: 64.9%) as a colorless oil. 1H NMR(400 MHz, DMSO-d6) deltappm; 1.67-1.82(5H, m), 3.35-3.42(2H, m), 3.49-3.57(4H, m), 3.65(2H, dd, J=7, 12 Hz), 3.86(2H, dd, J=4, 12 Hz), 4.56(1H, t, J=5 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4704-94-3, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US2007/10542; (2007); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 27489-62-9 , The common heterocyclic compound, 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: A solution of the desired intermediate 3a-l (0.07 mmol, 1 eq) in 1 mL DMSO was taken in a 5mL sealed reaction vessel, the corresponding amine (trans-4-aminocyclohexanol for 4a-k) (0.212 mmol, 3 eq) then diisopropylethylamine (DIPEA)(0.2l2 mmol, 3eq) was introduced. The reaction vessel was then sealed and heated to 140 C for 12 h, cooled and water (25 mL) was added. The aqueous layer was extracted with ethyl acetate (25 mL X 3), the organic fractions were combined and washed with brine (25mL) and dried over sodium sulfate. Purification with column chromatography (S1O2, 4:96 methanokDCM for 4a-k, 5a,5b,5e and 5: 1 :94 methanol :7M NH3 in methanokDCM for 5c,5d,5f,5g) resulted in the desired products which were further purified by preparative TLC to give the desired compounds 4a-k, 5a-g as light yellow solids. 8-(((lr,4r)-4-hydroxycyclohexyl)amino)-3-methyl-6-(3,6,6-trimethyl-4-oxo- 4,5,6,7-tetrahydro-lH-indazol-l-yl)isoquinolin-l(2H)-one (4a): 22 mg, Yield 70%; NMR (400 MHz, Chloroform -if) d 9.16 (d, J= 7.5 Hz, 1H), 9.05 (s, 1H), 6.51 – 6.40 (m, 2H), 6.09 (s, 1H), 3.74 – 3.59 (m, 2H), 3.31 (d, j= 24.2 Hz, 1H), 2.78 (s, 2H), 2.49 (s, 3H), 2.34 (s, 2H), 2.19 (s, 3H), 2.17 – 2.08 (m, 2H), 2.04 – 1.95 (m, 2H), 1.38 (q, 7= 11.1, 9.9 Hz, 4H), 1.04 (s, 6H). 13C NMR (101 MHz, CDCh) d 193.4, 185.3, 169.7, 165.5, 151.4, 150.0, 149.1, 143.5, 143.2, 142.1, 137.4, 107.3, 105.7, 104.8, 100.3, 69.7, 52.4, 50.2, 37.8, 35.8, 33.5, 29.9, 28.4 (2), 19.0, 13.4. HRMS (ESI) m/z [M+H] calculated for C26H33N4O3, 449.2553, found 449.2566.

The synthetic route of 27489-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF NOTRE DAME DU LAC; BLAGG, Brian; SANKET, Mishra; (0 pag.)WO2019/232223; (2019); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 4541-15-5, Adding some certain compound to certain chemical reactions, such as: 4541-15-5, name is 5-(Benzyloxy)pentan-1-ol,molecular formula is C12H18O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4541-15-5.

00193] 5-Benzyloxy-pentanoic acid (29)[00194] Jones reagent was added dropwise to an ice cooled solution of 5-benzyloxy-pentan- 1 – ol 28 (5 g, 25.74 mmol) in acetone (170 ml). Addition of the Jones reagent was stopped when the acetone solution acquired a persistent yellow color with the concurrent formation of green chromium salts. The mixture was filtered and concentrated in vacuo to give an oily crude product that was purified by a flash chromatography (EtOAc / hexanes, 1 :3) to give compound 29 (4.98 g, 93%) as a colorless oil: TLC R/= 0.68 (silica gel, 50% EtOAc / hexanes); 1HNMR (400 MHz, CDCl3) delta 7.35-7.31 (m, 5H), 4.502 (s, 2H), 3.51-3.47 (t,3J= 6 Hz, 2H), 2.41-2.36 (t, 3J= 6.8 Hz, 2H), 1.79-1.64 (m, 4H); 13C NMR (75 MHz, CDCl3) 5179.713, 138.651, 128.609, 127.870, 127.795, 73.158, 69.968, 33.915, 29.243, 21.749; HRMS calcd for C12H16O3 + Na+ 231.0997; found 231.0992 [M + Na+].

According to the analysis of related databases, 4541-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF TOLEDO; WO2007/15929; (2007); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 505-10-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 505-10-2 as follows.

24 g of PBr3 are mixed at 0 C., with stirring, with 20 g of 3-(methylsulphanyl)-1-propanol. The medium is allowed to return to AT and then it is heated at 100 C. for 1 hour. It is allowed to cool to AT and then it is cooled in an ice bath. The medium is taken up in benzene and then is extracted with toluene. The extract is washed with a 1% Na2CO3 solution, with water and then with a saturated NaCl solution. It is dried over MgSO4 and concentrated, and then distillation is carried out to produce 3.6 g of the expected compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,505-10-2, its application will become more common.

Reference:
Patent; Barth, Francis; Congy, Christian; Guillaumont, Carole; Rinaldi, Murielle; Vasse, Fabienne; Vernhet, Claude; US2004/34090; (2004); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts