Water → 3-(4-Azidomethyl-2-methyl-phenyl)-propionic Acid Methyl Ester

HRID 1785215Notes

Reaction equation

HRID 1785215 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]Cl)=[CH:8][C:7]=1[CH3:14].[N-:16]=[N+:17]=[N-:18].[Na+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:16]=[N+:17]=[N-:18])=[CH:8][C:7]=1[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 574319813-(4-Chloromethyl-2-methyl-phenyl)-propionic Acid Methyl Ester

Product 1

HCID 574319823-(4-Azidomethyl-2-methyl-phenyl)-propionic Acid Methyl EsterYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-Chloromethyl-2-methyl-phenyl)-propionic acid methyl ester (0.52 g, 2.31 mmol) in DMF (7 mL) is added sodium azide (0.25 g, 3.84 mmol). The mixture is stirred overnight. Water is added, and the mixture is extracted with EtOAc. The organics are dried with Na2SO4 and concentrated to yield the title compound (0.49 g, 91%). The material is used without further purification.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. dry with materialThe organics are dried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8d3e76129ce74d6693bb187128c35d37
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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