4-Toluenesulfonyl chloride → (R)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of (R)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol (108.96 g) in pyridine (550 ml) was added portionwise p-toluenesulfonyl chloride (129.66 g) at 10° C.~13° C. The reaction mixture was stirred at ambient temperature for 1 day. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate (1600 ml) and water (1080 ml). The organic layer was washed successively with 1N hydrochloric acid solution (1080 ml), aqueous sodium hydrogen carbonate (1080 ml), and brine (500 ml), dried over magnesium sulfate, and evaporated in vacuo to give a colorless powder. The colorless powder was washed with n-hexane (twice) to give (R)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl 4-methylbenzenesulfonate (182.23 g).

Provenance & Evidence