HCID 54224365, compound → (1R,4R,5S)-6,6-dimethyl-2-oxo-4-trichloromethyl-3-oxabicyclo[3.1.0]hexane

Participants

Reaction Steps

A solution of (1R)-3-methyl-1-trichloromethyl-2-butenyl diazoacetate (0.90 g, 3.33 mmole) from Example IA.4.(a) in 15 ml of dry dioxane was added dropwise over a period of 2.6 hours to a catalytic amount (approximately 2 mole %) of cupric acetylacetonate in 65 ml of refluxing dry dioxane under a nitrogen atmosphere. After refluxing for an additional hour, the mixture was evaporated, and an etheral solution of the residue was washed with 1 N HCl, saturated NaHCO3, and saturated NaCl, then dried over MgSO4 and evaporated to give (1R,4R,5S)-6,6-dimethyl-2-oxo-4-trichloromethyl-3-oxabicyclo[3.1.0]hexane (0.73 g, 90% crude yield) as a green-yellow oil.

Provenance & Evidence