HCID 18523498, compound → HCID 570659, compound

HRID 429176Notes

Reaction equation

HRID 429176 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 4 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 4 g of silica gel (230-400 mesh)
  2. washthe material eluted with ethyl acetate-methylene chloride

Sources & evidence

ORD record
ord-dfc8ad6d67ec47bbb98ccf6c478cf512
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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