Cornforth reagent → 2-(5-Oxohept-1-yl)bicyclo[3.3.0]octan-7-one

HRID 1789548Notes

Reaction equation

HRID 1789548 reaction equation
[OH:1][CH:2]([CH2:16][CH3:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2.[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]([CH2:16][CH3:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 15053004hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone3×

Product 1

HCID 150530192-(5-Oxohept-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 substituting the starting material from Example 3, 2-(5-hydroxyhept-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone} (2.0 g, 8.4 mmoles) and pyridinium dichromate (4.7 g, 12.6 mmoles) in methylene chloride (10 ml). The crude product is chromatographed on silica gel and subsequently kugelrohred under vacuum leaving a clear, colorless oil (1.7 g, 7.1 mmoles).

Workup

  1. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-5263750bf1284597acc5550363a196ee
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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