P5091 → 1-[5-(2,3-Dichlorophenyl)sulfanyl-4-nitro-2-thienyl]ethanol
Reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11][C:12]1[S:16][C:15]([C:17](=[O:19])[CH3:18])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21]>CO>[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11][C:12]1[S:16][C:15]([CH:17]([OH:19])[CH3:18])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium borohydride (54 mg, 1.44 mmol) was added to a suspension of 1-[5-(2,3-dichlorophenylsulfanyl)-4-nitro-2-thienyl]ethanone (0.5 g, 1.44 mmol) in methanol (10 mL) and the resulting mixture was stirred at ambient temperature. After 90 minutes, TLC showed no starting material remaining so the reaction was quenched by addition of water (20 mL). The resulting precipitate was collected by filtration and dissolved in dichloromethane (50 mL). The organic solution was dried over magnesium sulfate (MgSO4), filtered and the solvent removed to give a yellow solid. The crude solid was re-crystallized from methanol to afford the title product as a yellow solid (0.164 g, 33% yield). 1H NMR (300 MHz, CDCl3) δ: 7.65 (2H, m), 7.40 (1H, m), 7.33 (1H, t), 4.94 (1H, q), 1.99 (1H, d, J=4.74 Hz), 1.51 (3H, d, J=6.48 Hz).