Methyl iodide → Hydrochloric Acid

Participants

Reaction Steps

To a solution of 2.3 g of trans-8-bromo-7-methoxy-4-methyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine (Example 21) in 45 ml of tetrahydrofuran at -70° is added 5.6 ml of 2.6M t-butyllithium in hexane. After 5 minutes at -70°, 1.36 g of methyl iodide is added. After warming to 0°, the reaction mixture is diluted with ethyl acetate and washed with water. After drying over magnesium sulfate the solvent is removed in vacuo. Acidification of the residue with ethanolic hydrochloric acid yields trans-7-methoxy-4,8-dimethyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride, m.p. 277°-278°.

Provenance & Evidence