Cornforth reagent → tert-Butyl 6-oxohexylcarbamate

HRID 1758475Notes

Reaction equation

HRID 1758475 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]([O:26][C:27](=[O:36])[NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])([CH3:25])([CH3:24])[CH3:23]>ClCCl.C(OCC)C.CCCCC>[C:22]([O:26][C:27](=[O:36])[NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]=[O:35])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 4146612tert-Butyl N-(6-hydroxyhexyl)carbamate

Product 1

HCID 10536636tert-Butyl 6-oxohexylcarbamateYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21877078Diethylether pentaneSolvent

Procedure

Pyridinium dichromate (13.5 g, 0.036 mol) is added to a solution of t-butyl-(6-hydroxyhexyl)carbamate (5.88 g, 24 mmol) in dichloromethane (40 ml). After stirring for 24 hours, the reaction mixture is diluted with diethylether/pentane (1:1), filtered through Florisil and concentrated to yield t-butyl-(5-formylpentyl)carbamate (4.13 g, 80%).

Workup

  1. filtrationfiltered through Florisil
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4aa93656811145dfa786947a2e676a31
Source dataset
uspto-grants-1983_02
Patent number
US04374128

Reaction notes

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