Sodium borohydride → [3-Chloro-5-(2-hydroxymethyl-4-nitro-phenoxy)-phenyl]-acetic acid methyl ester

HRID 656755Notes

Reaction equation

HRID 656755 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]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58372717[3-Chloro-5-(2-formyl-4-nitro-phenoxy)-phenyl]acetic acid methyl ester

Product 1

HCID 58372735[3-Chloro-5-(2-hydroxymethyl-4-nitro-phenoxy)-phenyl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. customAfter work-up with EtOAc and H2O, the crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-abda9d7febe7448e8658473d585df7e4
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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