Cornforth reagent → 2-(3-Oxopent-1-yl)bicyclo[3.3.0]octan-7-one

HRID 1789559Notes

Reaction equation

HRID 1789559 reaction equation
[OH:1][CH:2]([CH2:14][CH3:15])[CH2:3][CH2:4][CH:5]1[CH2:12][CH2:11][CH:10]2[CH:6]1[CH2:7][C:8](=[O:13])[CH2:9]2.OC(CC)CCC1C(=O)CC2C1CCC2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:1]=[C:2]([CH2:14][CH3:15])[CH2:3][CH2:4][CH:5]1[CH2:12][CH2:11][CH:10]2[CH:6]1[CH2:7][C:8](=[O:13])[CH2:9]2

Participants

5

Reactant 3

HCID 2724130Cornforth reagentHCID 150530352-(3-Hydroxypent-1-yl)bicyclo[3.3.0]octan-7-one2×HCID 200287052-(3-Hydroxypent-1-yl)bicyclo[3.3.0]octan-3-one

Product 1

HCID 150530392-(3-Oxopent-1-yl)bicyclo[3.3.0]octan-7-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure followed is the same as that described in Example 13, making the following substitutions made: the starting material prepared in Example 31, 2-(3-hydroxypent-1-yl)bicyclo[3.3.0]octan-3-one {hexahydro-4-(3-hydroxypentyl)-2(1H)-pentalenone} (0.8 g, 3.8 mmoles), and pyridinium dichromate (0.82 g, 2.1 mmoles) dissolved in methylene chloride (10 ml). The crude product is chromatographed on silica gel and subsequently kugelrohred under reduced pressure leaving a clear, colorless oil (0.55 g, 2.6 mmoles).

Workup

  1. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-bd94112c7a234fb8bd6af3e52a8d474a
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

Loading…