HCID 54491600, compound → HCID 53964867, compound

HRID 1601329Notes

Reaction equation

HRID 1601329 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH:13]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:26])[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[O:12]=[C:13]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:26])[NH:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 54491600HCID 54491600, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 53964867HCID 53964867, compoundYield 819.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (15.28 g, 70.9 mmol) was added to a solution of phenyl-carbamic acid 4-hydroxy-4-phenyl-butyl ester (13.48 g, 4.73 mmol), prepared in the previous step, in 300 ml of methylene chloride and the mixture stirred at room temperature for 2.5 hours. The reaction was poured onto 700 g of a silica gel (230-400 mesh) column made with methylene chloride. Eluting with 0.5%-1.5% ethyl acetate-methylene chloride gave phenyl-carbamic acid 4-oxo-4-phenyl-butyl ester (10.98 g, 82%) as a white solid, mp 121-123° C.

Workup

  1. additionThe reaction was poured onto 700 g of a silica gel (230-400 mesh) column
  2. washEluting with 0.5%-1.5% ethyl acetate-methylene chloride

Sources & evidence

ORD record
ord-fd772d9de2f04d1fb7dfed1895d42d00
Source dataset
uspto-grants-1999_11
Patent number
US05977170

Reaction notes

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