Sodium borohydride → [3-Chloro-5-(2-hydroxymethyl-4-nitro-phenoxy)-phenyl]-acetic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[CH:21]=[O:22])[CH:8]=[C:7]([Cl:23])[CH:6]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[CH2:21][OH:22])[CH:8]=[C:7]([Cl:23])[CH:6]=1Participants
4
Procedure
To [3-chloro-5-(2-formyl-4-nitro-phenoxy)-phenyl]-acetic acid methyl ester (3.7 g, 10.6 mmol) in MeOH (30 mL) was added sodium borohydride (0.52 g, 13.8 mmol), and the reaction was stirred at room temperature for 20 minutes. After work-up with EtOAc and H2O, the crude material was purified by silica gel chromatography to give the title compound.