HCID 5073097, compound → HCID 70263997, compound

HRID 1004489Notes

Reaction equation

HRID 1004489 reaction equation
O[CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][NH:4][C:5](=[O:9])[CH:6]([CH3:8])[CH3:7].[Cr](Cl)([O-])(=O)=[O:17].[NH+]1C=CC=CC=1.C(OCC)(=O)C.C(Cl)Cl>C(Cl)Cl>[O:17]=[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:10]1[CH2:2][CH2:3][NH:4][C:5](=[O:9])[CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 5073097HCID 5073097, compoundHCID 21226138Dichloromethane ethylacetateHCID 178418287HCID 178418287, compound

Product 1

HCID 70263997HCID 70263997, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(2-hydroxy-2-phenyl-ethyl)-2-methyl-propanamide (15.0 g, 72 mmol), prepared in the previous step, and pyridinium chlorochromate (23.7 g, 110 mmol) in 300 ml of methylene chloride was stirred at room temperature for 5 hours. The reaction was filtered and the filtrate concentrated under reduced pressure to give a dark residue. Chromatography of the residue on silica gel (230-400 mesh) using ethyl acetate-methylene chloride as the eluent gave N-(2-oxo-phenyl-ethyl)-2-methyl-propanamide (6.07 g, 41%) as a light green solid, mp 88-93° C.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give a dark residue

Sources & evidence

ORD record
ord-3794661940d44993b32627d77b1b9cf0
Source dataset
uspto-grants-2000_04
Patent number
US06049006

Reaction notes

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