Electric Literature of 1994-13-4, 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.1994-13-4, name is 6-Fluoro-4-hydroxy-2H-chromen-2-one, molecular formula is C9H5FO3, molecular weight is 180.1326, as common compound, the synthetic route is as follows.
Compound 31: 8-Fluoro-3-(6-fluoro-4-hydroxy-2-oxo-2H-chromene-3-yl)-2-hydroxy- 2, 3-DIHYDRO-4H-FUROF3, 2-CLCHROMENE-4-ONE; Example 31; 6-Fluoro-4-hydroxycoumarin (180 mg; 1.0 mmole) was mixed with a 40 % aqueous solution of glyoxal (574 muL ; 5.0 mmole). Acetonitrile (8 mL) was added thereto and the reaction mixture was refluxed for 6 hours. By cooling the solution to room temperature a white precipitate was precipitated, which was filtered and washed with acetonitrile. There were obtained 62 mg (31 %) of compound 31, which did not need additional purification. 1H-NMR (300 MHz, DMSO-D6) No./PPM : 4. 85 (bs, 1H); 6.35 (bs, 1H); 7.40-7. 84 (m, 6H); 9.36 (bs, 1H); 3C-NMR (75.4 MHz, DMSO-D6) D/PPM : 42.8 ; 101.0 ; 101.6 ; 107.1 (D, J = 24.8 Hz) ; 108.1 (d, J = 25.7 Hz); 108. 6; 111.9 (d); 115.9 (d); 117.4 (d); 117.8 (d); 118.7 (d, J = 23.0 Hz); 119.0 (d, J= 20 Hz); 147.4 ; 149.7 ; 156.7 (d, 241 Hz); 158. 1 (d, 236 Hz); 160.2 ; 162.2 ; 163.1 ; 165.4 ; MS m/z : ES- (acetonitrile: water) [M-H]-: 399.0.
The chemical industry reduces the impact on the environment during synthesis 1994-13-4, I believe this compound will play a more active role in future production and life.
Reference:
Patent; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2005/10006; (2005); A1;,
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