Sodium borohydride → [3-(2-Hydroxymethyl-phenoxy)-phenyl]-acetic acid ethyl ester

HRID 885224Notes

Reaction equation

HRID 885224 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]=[O:20])[CH:7]=1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][OH:20])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58237581[3-(2-Formyl-phenoxy)-phenyl]-acetic acid ethyl ester

Product 1

HCID 58237647[3-(2-Hydroxymethyl-phenoxy)-phenyl]-acetic acid ethyl esterYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To [3-(2-formyl-phenoxy)-phenyl]-acetic acid ethyl ester (1.0 g, 3.5 mmol) in MeOH (20 mL) was added sodium borohydride (0.16 g, 4.2 mmol), and the reaction was stirred for 10 minutes at room temperature. Once no starting material was seen by analytical tlc, the mixture was worked-up to give the desired product (1 g).

Sources & evidence

ORD record
ord-8a14d2fbff084c62893f17362a3dbb88
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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