Potassium Carbonate → N-[4-Methyl-2-(2-oxiranylmethoxy)phenyl]acetamide

HRID 1072493Notes

Reaction equation

HRID 1072493 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:12])[CH3:11].Br[CH2:14][CH:15]1[CH2:17][O:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]([NH:9][C:10](=[O:12])[CH3:11])=[C:2]([O:1][CH2:14][CH:15]2[CH2:17][O:16]2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 83437N-(2-Hydroxy-4-methylphenyl)acetamide

Product 1

HCID 22386970N-[4-Methyl-2-(2-oxiranylmethoxy)phenyl]acetamideYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of N-(2-hydroxy-4-methylphenyl)acetamide (10 g, 60 mmol), 2-(bromomethyl)oxirane (9.86 g, 72 mmol, 6.0 ml) and potassium carbonate (16.8 g, 120 mmol) in DMF (100 ml) was heated at 55° C. for 2 h. Then the reaction mixture was diluted with ethyl acetate and washed with aq. HCl (1.5%), aq. sat. NaHCO3, and brine. Evaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (ethyl acetate from 35 to 70%) afforded the title compound (5.65 g, 25 mmol, 43%).

Workup

  1. washwashed with aq. HCl (1.5%), aq. sat. NaHCO3, and brine
  2. customEvaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (ethyl acetate from 35 to 70%)

Sources & evidence

ORD record
ord-71c2b4084c3d46c1830494e2434f7bf9
Source dataset
uspto-grants-2005_06
Patent number
US06911458B2

Reaction notes

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