Sodium Chloride → 3-(4-Carboxybutylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octane

Participants

Reaction Steps

An ylide solution was prepared from 440 g of triphenyl (4-carboxybutyl)phosphonium bromide and sodium dimsyl (prepared from 75.0 g of a 55% w/w suspension of sodium hydride in oil and 3 liters of dimethyl sulfoxide) in dimethyl sulfoxide. To this were added dropwise 36.0 g of 7,7-ethylenedioxy-3-oxo-cis-bicyclo[3,3,0]octane in 400 ml of dimethyl sulfoxide, and the mixture was left standing at room temperature for 48 hours under an atmosphere of nitrogen. Upon completion of the reaction, the reaction product was neutralized with acetic acid, and the mixture was poured into a saturated aqueous solution of sodium chloride. The mixture was extracted with ethyl acetate, and the extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, giving 164.3 g of residue. On purifying the residue by column chromatography through silica gel, 49.10 g of the title compound was obtained in the form of an oil, from the fractions eluted with hexane containing 30-40% by volume of ethyl acetate.

Provenance & Evidence