(1S,3S)-3-(Hydroxymethyl)-2,2-dimethylcyclopropane-1-carboxylic acid → (1r,5s)-6,6-Dimethyl-3-oxabicyclo[3.1.0]hexan-2-one

Participants

Reaction Steps

From 4041 g of the resultant solution, 20.1 g of that was used, and the subsequent cis body/trans body separation operation was carried out. Into 20.1 g of this solution, a 20% sodium hydroxide aqueous solution was dropped, to adjust pH of the solution to 3. An extraction operation was repeated three times from this solution with 7.8 kg of toluene, and the resultant organic layers were combined. Then, toluene was distilled off, then, 1.49 g of a solution containing 1.17 g of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one (9.27 mmol, yield based on ethyl cis-3-acetoxymethyl-2,2-dimethylcyclopropanecarboxylate: 97.2%, (1R, 5S)-body had an optical purity of 92.8% ee) was obtained. In this toluene solution, 0.057 g (0.39 mmol) of trans-3-hydroxymethyl-2, 2-dimethylcyclopropanecarboxylic acid was present.

Provenance & Evidence