Sodium borohydride → HCID 11596162, compound

Reaction equation

[BH4-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([S:19]([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH:24]=[O:25])(=[O:21])=[O:20])=[CH:15][CH:14]=1>CO.C(Cl)Cl>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1/[CH:11]=[CH:12]/[C:13]1[CH:14]=[CH:15][C:16]([S:19]([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH2:24][OH:25])(=[O:20])=[O:21])=[CH:17][CH:18]=1

Participants

Procedure

Sodium borohydride (89 mg, 1.8 mmol) was added to a solution of 2-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)benzaldehyde (Step 1; 233 mg, 0.61 mmol) in MeOH (7 mL) and CH2Cl2 (3 mL). After 2 h, the mixture was partitioned between CH2Cl2 (10 mL) and water (10 mL), the phases were separated and the aqueous portion extracted with further CH2Cl2 (10 mL). The combined organics were then dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant 40% EtOAc/isohexane) gave the title compound as a white solid (208 mg). δH (500 MHz, d6 DMSO): 8.08 (1H, d, J 7.7), 7.89-7.83 (5H, m), 7.77 (1H, d, J 7.6), 7.72 (1H, t, J 7.4), 7.55 (1H, t, J 7.5), 7.42-7.34 (2H, m), 7.33-7.27 (1H, m), 7.15 (1H, td, J 2.1, 8.4), 5.39 (1H, t, J 5.7), 4.69 (2H, d, J 5.7). m/z (ES+) 369 [(M-OH)+].