Acetic Acid → 2-(3-Hydroxypent-1-yl)bicyclo[3.3.0]octan-7-one

HRID 1789553Notes

Reaction equation

HRID 1789553 reaction equation
Cl[C:2]1(Cl)[C:8](=[O:9])[CH:7]2[CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:10][CH2:11][CH:12]([O:15][Si](C(C)(C)C)(C)C)[CH2:13][CH3:14].[C:24](O)(=O)C>[Zn]>[OH:15][CH:12]([CH2:13][CH3:14])[CH2:11][CH2:10][CH:6]1[CH2:5][CH2:4][CH:3]2[CH:7]1[CH2:24][C:8](=[O:9])[CH2:2]2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 142041096,6-Dichloro-2-(3-[(1,1-dimethylethyl)dimethylsiloxy]pent-1-yl)bicyclo[3.2.0]heptan-7-one

Product 1

HCID 150530352-(3-Hydroxypent-1-yl)bicyclo[3.3.0]octan-7-one

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

The procedure followed is the same as that described in Example 11 substituting the starting material prepared in Example 28, 6,6-dichloro-2-(3-[(1,1-dimethylethyl)dimethylsiloxy]pent-1-yl)bicyclo[3.2.0]heptan-7-one {7,7-dichloro-4-[3,[[(1,1-dimethylethyl)dimethylsilyl]oxy]pentyl]bicyclo[3.2.0]heptan-6-one} and isomers (2.4 g, 6.1 mmoles), glacial acetic acid (17 ml), and zinc powder (5 g). The crude product is chromatographed on silica gel and subsequently kugelrohred under vacuum leaving a clear, colorless oil (1.0 g, 4.8 mmoles).

Workup

  1. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-543ea79e85d34e10aec88caf76c63806
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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