Hydrochloric Acid → HCID 67939631, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.865 g (0.0031 mol) of 3-(4-chlorophenyl)-4,5,6,7-tetrahydro-1,2-benzisoxazole-6-carboxylic acid in 20 ml of dry tetrahydrofuran was added slowly at -70° C. to a solution of lithium diisopropylamide prepared by adding 2.65 ml of a 2.5M solution of n-butyllithium in hexane to 0.66 g (0.0065 mol) of diisopropylamine in 20 ml of dry tetrahydrofuran at -70° C. After 0.25 hour a deep red solution had formed. 0.53 g (0.0031 mol) of isopropyl iodide in 5 ml of dry tetrahydrofuran was added and the mixture was stirred at -65° C. to -30° C. for 1 hour and at a temperature up to 5° C. for an additional 1 hour. The resulting yellow solution was poured into an excess of water and acidified with 2N hydrochloric acid. The mixture was extracted four times with diethyl ether and the combined ether extracts were washed with sodium chloride solution and dried over magnesium sulfate. Evaporation gave a yellow solid which, after crystallization from glacial acetic acid, yielded 0.53 g of trans-3-(4-chlorophenyl)-4,5,6,7-tetrahydro-7-isopropyl-1,2-benzisoxazole-6- -carboxylic acid of melting point 180°-182° C.

Provenance & Evidence