Cornforth reagent → HCID 20158426, compound

HRID 986334Notes

Reaction equation

HRID 986334 reaction equation
[OH:1][C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][CH:5]([OH:7])[CH:4]=[CH:3]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[OH:1][C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:6][C:5](=[O:7])[CH:4]=[CH:3]1

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 20158400HCID 20158400, compound

Product 1

HCID 20158426HCID 20158426, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1.9 g (7.6 mmoles) of 3,5-dihydroxy-3-(4-phenoxybutyl)cyclopentene was dissolved in 15 ml of dichloromethane, and at 0° C. 5.7 g (15 mmoles) of pyridinium dichromate was added. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with 200 ml of ether, and filtered through Celite. After concentration, 1.32 g (71%) of 4-hydroxy-4-(4-phenoxybutyl)-2-cyclopentenone was obtained.

Workup

  1. customat 0° C
  2. filtrationfiltered through Celite
  3. concentrationAfter concentration

Sources & evidence

ORD record
ord-937378dd8ac1455c83462ec90b4afd46
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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