HCID 18523505, compound → HCID 18523497, compound

HRID 429178Notes

Reaction equation

HRID 429178 reaction equation
[CH:1]1([NH:7][C:8](=[O:19])[CH2:9][CH2:10][CH:11]([OH:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:1]1([NH:7][C:8](=[O:19])[CH2:9][CH2:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 18523505HCID 18523505, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18523497HCID 18523497, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-cyclohexyl-4-hydroxy-4-phenyl-butyramide (3.98 g, 15.2 mmol), prepared in the previous step, and pyridinium chlorochromate (4.94 g, 22.9 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 methylene chloride-ethyl acetate. Isolation of the major component gave N-cyclohexyl-4-oxo-4-phenyl-butyramide (3.28 g, 83%) as a light green solid, mp 109-111° C.

Workup

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

Sources & evidence

ORD record
ord-6d4464aa11fc44fe8fdcd81caac33813
Source dataset
uspto-grants-2001_11
Patent number
US06316467B1

Reaction notes

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