Hydrochloric Acid → HCID 67896168, compound

Participants

Reaction Steps

A solution of 1.73 g (0.00625 mol) of 3-(4-chlorophenyl)-4,5,6,7-tetrahydro-1,2-benzisoxazole-6-carboxylic acid in 30 ml of dry tetrahydrofuran was added slowly at -70° C. to a solution of lithium diisopropylamide prepared by adding 5.25 ml of a 2.5M solution of n-butyllithium in hexane to 1.32 g (0.013 mol) of diisopropylamine in 20 ml of dry tetrahydrofuran at -70° C. After 0.25 hour a deep red color had developed. 1.05 g (0.0067 mol) of ethyl iodide in 5 ml of dry tetrahydrofuran were added and the temperature was allowed to rise to -20° C. over a period of 1.25 hours. The resulting light brown 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, dried over magnesium sulfate and evaporated. The residue was crystallized twice from glacial acetic acid and there was obtained 0.36 g of trans-3-(4-chlorophenyl)-7-ethyl-4,5,6,7-tetrahydro-1,2-benzisoxazole-6-carboxylic acid of melting point 162°-163° C.

Provenance & Evidence