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

HRID 860652Notes

Reaction equation

HRID 860652 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-5304e71abee043bd9ca98bd9be0a0fa4
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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