Methanol → Sodium 7-(4-fluorophenyl)quinoline-3-sulfinate

반응식

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([S:18](CCC(OC)=O)(=[O:20])=[O:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CO.C[O-].[Na+:31]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([S:18]([O-:20])=[O:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[Na+:31]

참가 물질

실험 절차

Methyl 3-{[7-(4-fluorophenyl)quinolin-3-yl]sulfonyl}propanoate (4.23 g, 11.3 mmol) was dissolved/suspended in hot tetrahydrofuran (240 mL). Methanol (60 mL) was added and the mixture allowed to cool to about 30° C., at which point sodium methoxide (0.91 g, 17 mmol) was added and the resulting mixture stirred for 1 hour. The solid present was collected under suction, washed with tetrahydrofuran and dried in vacuo to afford a first crop of sodium 7-(4-fluorophenyl)quinoline-3-sulfinate (2.1 g). The filtrate was concentrated and the residue triturated with tetrahydrofuran. The solid was collected under suction, washed successively with small volumes of tetrahydrofuran, ice-cold water then tetrahydrofuran, and dried in vacuo to give a second crop of product (0.87 g). The combined yield of the title product was 2.97 g (85%). 1H NMR (500 MHz, CD3OD) δ 9.13 (1H, d, J 1.9 Hz), 8.52 (1H, d, J 1.6 Hz), 8.24 (1H, s), 8.11 (1H, d, J 8.5 Hz), 7.94 (1H, dd, J 1.7, 8.5 Hz), 7.84-7.82 (2H, m), 7.26 (2H, t, J 8.7 Hz).