Triethylamine → 2-(2-Thienyl)ethyl methanesulphonate

Participants

Reaction Conditions

Reaction Steps

To a flask was added 25.6 g. (0.20 mole) of 2-(2-thienyl)ethanol in 75 ml. of THF followed by 40.47 g. (0.40 mole) of triethylamine in 30 ml. of THF. The mixture was cooled to 5° C. and 34.4 g. (0.3 mole) of methanesulfonyl chloride in 20 ml. of THF was added dropwise over 20 minutes. The mixture exothermed to 20° C. and was kept at 20° C. during the methanesulfonyl chloride addition. An additional 150 ml. of THF was added to reduce the viscosity of the mixture after a precipitate had formed. After two hours, the reaction was quenched by the addition of 25 ml. of water which was followed by 25 ml of 10% aqueous hydrochloric acid and 200 ml. of ether. The ether layer was separated, washed with 50 ml. of 10% aqueous hydrochloric acid and twice with 75 ml. of saturated aqueous sodium bicarbonate solution, dried, and concentrated to give the 2-(2-thienyl)ethyl methanesulfonate, 38.0 g. (92.2% yield), as an oil.

Provenance & Evidence