McBee, E. T. published the artcileThe preparation and properties of some compounds containing the 4,4,4-trifluorocrotyl group, COA of Formula: C4H5F3O, the publication is Journal of the American Chemical Society (1954), 3725-8, database is CAplus.
The preparation and reactions of several compounds containing the CF3CH:CHCH2 group are described, and an unusual reaction of LiAlH4, the reduction of CF3CHBrCHBrCO2Et (I) to CF3CH:CHCH2OH (II) at about -80°, is reported. CF3CH:CHCO2Et (IIa) (76 g.) in 150 cc. CCl4 refluxed, the mixture treated dropwise with 90 g. Br with the occasional addition of 150 cc. CCl4 in portions to keep the Br in solution, the mixture refluxed 24 hrs. while illuminating with a 100-watt bulb, the excess Br and CCl4 distilled off at atm. pressure, the residue distilled, b15 65-92°, and the distillate rectified yielded 125 g. (84.5%) I, b15 90.0-2.0°, n20D 1.4448, d25 1.823. I treated with PhCH2NH2 (III) gave only III. HBr, m. 220°. CF3CH:CHCO2H (IV) (20 g.) and 60 g. BzCl slowly heated to 195° while distilling the acid chloride from the mixture, and the distillate, b. 64-72°, rectified gave 11.5 g. (50%) CF3CH:CHCOCl (V), m. 77.0-7.5°, n20D 1.3703, d25 1.362; it gave with MeNH2 the N-Me amide of IV, m. 110°. BzCl (300 g.)treated with IV at 150-60° (obtained as the residue from the acidolysis of 100 g. IIa with HCO2H) dropwise while slowly distilling the acid chloride from the reactor, the residual mixture treated with 100 g. BzCl and heated until no more chloride distilled, and the crude distillate rectified yielded 65.0 g. (67%) V. CF3CH(OH)CH2CO2Et (46.5 g.) in an equal volume Et2O added dropwise with cooling during 0.5 hr. to 12.0 g. LiAlH4 in 200 cc. dry Et2O, the mixture stirred 12 hrs. at room temperature, the excess hydride destroyed with 95% EtOH, the mixture treated with 50 cc. concentrated H2SO4 and 250 g. ice, the acid layer extracted twice with 100-cc. portions Et2O, the combined organic layer and extract distilled, and the residue dried azeotropically with C6H6 and distilled yielded 30 g. (83%) CF3CH(OH)CH2CH2OH, b20 104-5°, viscous cloudy liquid which solidified during several hrs. at 0° to give a white, crystalline and deliquescent solid. I (163 g.) in 200 cc. Et2O added dropwise with stirring at about -80° to 20 g. LiAlH4 in 400 cc. dry Et2O, the mixture stirred 20 hrs. at about -80°, the excess hydride destroyed with 95% EtOH, the reaction complex poured into 100 cc. concentrated H2SO4 and 1 kg. ice, the acid layer washed with two 100-cc. portions Et2O, the combined organic layer and extract dried with Drierite and evaporated, the residue dried azeotropically with 25 cc. C6H6 and distilled, and the distillate, b28 35-54° rectified yielded 33.0 g. (50%) II, b. 128.0-8.5°, n20D 1.3578, d25 1.256; phenylurethan, m. 63.0°. B(OMe)3 (73.0 g.) added dropwise to 18.0 g. NaH in 750 cc. dry, refluxing tetrahydrofuran, the mixture refluxed 2 hrs., cooled, let settle, and filtered under N pressure through glass wool, the filtrate treated with 52.0 g. V in 150 cc. dry tetrahydrofuran, the mixture stirred 2 hrs., treated cautiously with H2O, and poured into 50 cc. concentrated H2SO4 and 1 kg. ice, the resulting homogeneous solution extracted with about 1500 cc. Et2O in portions, the extract dried with Na2SO4, the solvents distilled off, and the residue rectified yielded 12.0 g. (33%) II. IIa (33.5 g.) in an equal volume Et2O added with cooling during 1 hr. to iso-PrMgBr from 74 g. iso-PrBr and 14.4 g. Mg, the mixture hydrolyzed with ice-cold 10% aqueous H2SO4, and the product rectified yielded 17.0 g. (40%) Me2CHCH(CF3)CH2CO2Et, b65 98.0-9.0°, n20D 1.3850, d25 1.113; Me2CHCH(CF3)CH2CO2NHNH2, m. 41.0°; apparently this is the m.p. of a hydrate; after drying in an Abderhalden pistol over P2O5 the material turned liquid in air, then solidified to the 41.0° material; Me2CHCH(CF3)CH2CONHPh, m. 129.0°. IIa (33.5 g.) added to EtMgI from 93 g. EtI and 14.4 g. Mg, the mixture hydrolyzed with saturated aqueous NH4Cl, the aqueous layer extracted with Et2O, and the combined organic layer and extract distilled gave 15.9 g. (40%) CF3CHEtCH2CO2Et, b25 62.0-5.0°, n20D 1.3750, d25 1.110. Freshly distilled (iso-PrO)3Al (5.5 g.) and 10 g. II heated slowly at 65-70° and 100 mm. pressure, the mixture kept 1 hr. at this temperature while slowly distilling off some iso-PrOH, heated to 110° to remove all iso-PrOH, and distilled at 20 mm. to remove 1.3 g. II, the residue treated at 65° and 100 mm. dropwise with 16.3 g. p-MeOC6H4CHO, and the mixture distilled gave 3.0 g. CF3CH:CHCHO, clear, water white liquid, b70 70-6°; 2,4-dinitrophenylhydrazone, m. 226.0°.
Journal of the American Chemical Society published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, COA of Formula: C4H5F3O.
Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts