Ammonium Chloride → Ethyl alpha,alpha-dichloro-6,6-dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexane-2-acetate

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Reaction Conditions

Reaction Steps

A solution of ethyl α,α,3-trichloro-3,4,5,6-tetrahydro-4,4-dimethyl-6-oxo-2H-pyran-2-acetate (3.43 g, 10.8 mmol) in 20 ml of tetrahydrofuran was cooled to -20° C. Potassium tert-butoxide was added in small portions while the mixture was stirred and maintained at -20° C. over a period of two hours. A total of 1.4 g (12.5 mmol) was added. Aqueous ammonium chloride was added and the mixture was extracted with methylene chloride. Purification by column chromatography gave 1.82 g of ethyl α,α-dichloro-6,6-dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexane-2-acetate (60% yield).

Provenance & Evidence