HCID 19352254, compound → HCID 10488465, compound

HRID 1636634Notes

Reaction equation

HRID 1636634 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19]>C(Cl)Cl>[O:12]=[C:13]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 19352254HCID 19352254, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 10488465HCID 10488465, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (10.08 g, 46.8 mmol) was added to a solution of N-(4-hydroxy-4-phenyl-butyl)-acetamide (6.46 g, 31.2 mmol), prepared in the previous step, in 200 ml of methylene chloride and the mixture stirred at room temperature for 1.5 hours. The entire reaction mixture was poured onto 200 g of silica gel (230-400 mesh) and the material eluted with ethyl acetate. Isolation of the major fraction gave N-(4-oxo-4-phenyl-butyl)-acetamide (4.35 g, 68%) as a light brown solid, mp 92-95° C.

Workup

  1. customThe entire reaction mixture
  2. additionwas poured onto 200 g of silica gel (230-400 mesh)
  3. washthe material eluted with ethyl acetate

Sources & evidence

ORD record
ord-286f016d036a45a0a65c05084a1a82ea
Source dataset
uspto-grants-2000_03
Patent number
US06034272

Reaction notes

Loading…