Trimethylamine → 1,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

The crude oil, 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol, from Example 5 is dissolved in 250 ml of methylene chloride and cooled to 10° C. Then 12.2 g of trimethylamine is added and the reaction mixture is cooled to about 5° C. Over a 15 minute period, 10.55 g of methanesulfonyl chloride is added. The reaction mixture is stirred for about 30 minutes at 0°-5° C. Separation of the triethylamine hydrochloride as a precipitate is observed. The reaction mixture then is poured into 200 ml of water and extracted with methylene chloride. The organic phase is separated, dried over magnesium sulfate and evaporated under reduced pressure to yield 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate as an oil.

Provenance & Evidence