HCID 18523506, compound → HCID 18523504, compound

HRID 413206Notes

Reaction equation

HRID 413206 reaction equation
[CH3:1][CH:2]([NH:9][C:10](=[O:21])[CH2:11][CH2:12][CH:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][CH:2]([NH:9][C:10](=[O:21])[CH2:11][CH2:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 18523506HCID 18523506, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18523504HCID 18523504, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(1,5-dimethyl-hexyl)-4-hydroxy-4-phenyl-butyramide (3.50 g, 12.0 mmol), prepared in the previous step, and pyridinium chlorochromate (3.89 g, 18.0 mmol) in 150 ml of methylene chloride was stirred at room temperature for 1.25 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-(1,5-dimethyl-hexyl)-4-oxo-4-phenyl-butyramide (2.71 g, 78%) as a light green solid, mp 84-87° 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-b14c87c3876d443ab3f71dfc80a4de52
Source dataset
uspto-grants-2003_05
Patent number
US06566375B1

Reaction notes

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