epsilon-CAPROLACTONE → 3-Methylideneoxepan-2-one

HRID 259762Notes

Reaction equation

HRID 259762 reaction equation
[C:1]1(=[O:8])[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1(SCCl)C=CC=CC=1.I([O-])(=O)(=O)=O.[Na+]>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[CH2:9]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:1]1=[O:8]

Participants

6

Reactant 3

HCID 10401epsilon-CAPROLACTONEHCID 81623Chloromethyl phenyl sulphideHCID 23667635Sodium periodate

Product 1

HCID 131134793-Methylideneoxepan-2-one

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

This synthesis was carried out by reaction of the silyl enol of ε-caprolactone with chloromethyl phenyl sulphide in the presence of a catalytic amount of zinc chloride to give the sulphurized compound, which was oxidized into sulphoxide using sodium metaperiodate. Pyrolysis of the sulphoxide in refluxing toluene gave α-methylene-ε-caprolactone.

Workup

  1. customto give the sulphurized compound, which

Sources & evidence

ORD record
ord-673836dd637b4cba93128baaa857e635
Source dataset
uspto-grants-1996_06
Patent number
US05523319

Reaction notes

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