HCID 18523498, compound → HCID 570659, compound

HRID 413200Notes

Reaction equation

HRID 413200 reaction equation
[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][C:5]([NH:7][CH3:8])=[O:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:8][NH:7][C:5](=[O:6])[CH2:4][CH2:3][C:2](=[O:1])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 18523498HCID 18523498, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 570659HCID 570659, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxy-N-methyl-4-phenyl-butyramide (4.50 g, 23.3 mmol), prepared in the previous step, and pyridinium chlorochromate (7.54 g, 35.0 mmol) in 200 ml of methylene chloride was stirred at room temperature for 2.5 hours. The reaction was poured onto 400 g of silica gel (230-400 mesh) and the material eluted with ethyl acetate-methylene chloride and then ethyl acetate. Isolation of the major component gave N-methyl-4-oxo-4-phenyl-butyramide (3.65 g, 82%) as an off-white solid, mp 80-82° C.

Workup

  1. additionThe reaction was poured onto 400 g of silica gel (230-400 mesh)
  2. washthe material eluted with ethyl acetate-methylene chloride

Sources & evidence

ORD record
ord-ddddb836f39b4e828873fe1fb0b086a0
Source dataset
uspto-grants-2003_05
Patent number
US06566375B1

Reaction notes

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