Methyl iodide → HCID 19899024, compound

Participants

Reaction Conditions

Reaction Steps

3.06 g (0.01 mol) of methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-cyclohept[d]isoxazole-6-carboxylate in 20 ml of dry tetrahydrofuran were added at -70° C. to a solution of lithium diisopropylamide prepared by adding 6 ml of a 2.5M solution of n-butyllithium in hexane over a period of 0.25 hour to a solution of 1.5 g (0.01015 mol) of diisopropylamine in 40 ml of tetrahydrofuran at -70° C. After stirring for 0.5 hour, 2.13 g (0.015 mol) of methyl iodide in 5 ml of tetrahydrofuran were added and the mixture was allowed to warm to 10° C. over a period of 0.5 hour. The mixture was added to ice/water and extracted three times with diethyl ether. The extracts were washed with sodium chloride solution to give 4.4 g of crude product which was purified by column chromatography on silica gel using hexane/diethyl ether for the elution. There were obtained 1.58 g of methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-6-methyl-4H-cyclohept[d]isoxazole-6-carboxylate; NMR: δ CDCl3 : 7.35 (m, 4H), 3.6 (s, 3H), 2.85 (m, 2H), 2.47 (m, 2H), 2.15 (m, 2H), 1.6 (m, 2H), 1.2 (3H).

Provenance & Evidence