Hydrochloric Acid → Z-5,6,7,8-Tetrahydro-4-methyl-8-(1-(4-methylphenyl)ethylidene)quinoline

Participants

Reaction Conditions

Reaction Steps

5,6,7,8-Tetrahydro-4-methylquinoline (7.5 g) in tetrahydrofuran (THF) (25 ml) was added to a solution of n-butyl lithium (1.37M, 37 ml) in THF (40 ml) maintained at 0° C. After 30 minutes the solution was blown over with nitrogen onto a solution of trimethylsilyl chloride (5.6 g) in THF (25 ml) at 0° C. Further n-butyl lithium (1.37M, 37 ml) was added and after 30 minutes the reaction mixture was blown over with nitrogen onto 4-methylacetophenone (15 g) in THF (25 ml) at 0° C. After 10 minutes 2M HCl (150 ml) was added.

Provenance & Evidence