HCID 19352255, compound → HCID 19352253, compound

HRID 1636631Notes

Reaction equation

HRID 1636631 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH:13]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:14][CH2:15][CH2:16][N:17]([CH:21]([CH3:23])[CH3:22])[C:18](=[O:20])[CH3:19]>C(Cl)Cl>[CH:21]([N:17]([CH2:16][CH2:15][CH2:14][C:13](=[O:12])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18](=[O:20])[CH3:19])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 19352255HCID 19352255, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 19352253HCID 19352253, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (20.35 g, 94.2 mmol) was added to a solution of N-(4-hydroxy-4-phenyl-butyl)-N-isopropyl-acetamide (15.69 g, 62.9 mmol), prepared in the previous step, in 350 ml of methylene chloride and the mixture stirred at room temperature for 2 hours. The entire reaction mixture was poured onto 750 g of silica gel (230-400 mesh) and the material eluted with 50% ethyl acetate-methylene chloride and then ethyl acetate. Isolation of the major fraction gave N-isopropyl-N-(4-oxo-4-phenyl-butyl)-acetamide (12.43 g, 80%) as a green solid, mp 36-39° C.

Workup

  1. customThe entire reaction mixture
  2. additionwas poured onto 750 g of silica gel (230-400 mesh)
  3. washthe material eluted with 50% ethyl acetate-methylene chloride

Sources & evidence

ORD record
ord-969243fb3bfd409cbc60006e939e8de7
Source dataset
uspto-grants-2000_03
Patent number
US06034272

Reaction notes

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