Water → Methyl 6-(3-carboxybicyclo[2.2.1]hept-2-yl)-hex-5-enoate

Participants

Reaction Conditions

Reaction Steps

A solution of 25.0 g (0.1 mole) of methyl 6-(3-hydroxymethyl-bicyclo[2.2.1]hept-2-yl)-hex-5-enoate in 60 ml of absolute dimethylformamide is added to 132.0 g (0.35 mole) of pyridinium dichromate in 200 ml of absolute dimethylformamide at 20° C. The reaction mixture is stirred at 20° C. for 9 hours, left to stand for 14 hours and then poured into 1.9 liters of water and extracted with diethyl ether. After drying over Na2SO4, the mixture is evaporated in vacuo and the residue is chromatographed on silica gel, using methylene chloride/methanol (95:5) to give 17.3 g of methyl 6-(3-carboxy-bicyclo-[2.2.1]hept-2-yl)-hex-5-enoate (yield: 65%)

Provenance & Evidence