Methyl iodide → 2-(3-Benzyloxy-5-trifluoromethyl-phenyl)-propionic acid ethyl ester

HRID 563556Notes

Reaction equation

HRID 563556 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=1)[CH3:2].[H-].[Na+].I[CH3:28]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([C:6]1[CH:11]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:9]=[C:8]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=1)[CH3:28])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58148866(3-Benzyloxy-5-trifluoromethyl-phenyl)-acetic acid ethyl ester

Product 1

HCID 574587982-(3-Benzyloxy-5-trifluoromethyl-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-benzyloxy-5-trifluoromethyl-phenyl)-acetic acid ethyl ester (5.0 g, 14.8 mmol) in DMF (50 mL) at 0° C. under N2 was added sodium hydride (60% in mineral oil; 0.65 g, 16.3 mmol), and the mixture was stirred at room temperature for 15 minutes. Iodomethane (1 mL, 16.3 mmol) was added, and the reaction was monitored by analytical LCMS and tlc. 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-42238717f35e4a82906b10359b825948
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

Loading…