Sodium hydride → HCID 54450935, compound

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Reaction Steps

12 g (0.4 mole) of 80% strength NaH are added to 240 ml of absolute dimethylsulphoxide under an inert gas, and the mixture is warmed at 60° to 70° C. until the evolution of hydrogen has ended. Thereafter, 88.4 g (0.2 mole) of 4-carboxybutyl-triphenyl-phosphonium bromide in 200 ml of absolute dimethylsulphoxide are added at 15° to 16° C. After the mixture has been subsequently stirred for 10 minutes, 15.4 g (0.1 mole) of 1-hydroxyoctahydro-4,7-methano-iso-benzofuran in 50 ml of absolute dimethylsulphoxide are allowed to run in and the mixture is stirred at 20° C. for 3 hours. 20 ml of water are then added, the solvent is distilled off in vacuo and the evaporation residue is partitioned between 200 ml of water and 4×400 ml of diethyl ether. The aqueous phase is brought to pH 3.5 with 5N hydrochloric acid and the precipitate which deposits is separated off and washed 3, times with 200 ml of diethyl ether. The aqueous phase which remains is saturated with sodium chloride and extracted 5 times with 200 ml of diethyl ether. After the combined ethereal extracts have been dried, the solvent is evaporated off in vacuo and the residue is chromatographed on silica gel using methylene chloride/tetrahydrofuran/acetic acid (10:1:0.5). 30.9 g of 6-(3-hydroxymethylbicyclo[2.2.1]-hept-2-yl)-hex-5-enoic acid are obtained in this manner (65% yield).

Provenance & Evidence