Benzene → HCID 57166467, compound

Participants

Reaction Conditions

Reaction Steps

25 g of (1R, 2S)-2-methoxycarbonylcyclohex-4-ene-1-carboxylic acid and 40 ml of thionyl chloride were dissolved in 200 ml of dry benzene, and the mixture was refluxed for two hours. The solvent was distilled off under a reduced pressure, and to the residue was added ml of dried tetrahydrofuran. Further, 1.29 g of copper (I) iodide was added to the solution, which was cooled to -5° C, 182 ml of tetrahydrofuran solution of methylmagnesium bromide (0.82M) was added dropwise to the solution over a period of 1.5 hours. The solution was further stirred for one hour at the same temperature, and then 1N-hydrochloric acid was added. After the organic layer was separated, the water layer was extracted with ether. The organic layer was successively washed with 5% sodium thiosulfate solution, saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate: hexane=15:85) to be purified, and thus 18.27 g of the titled compound was obtained.

Provenance & Evidence