Water → Pentan-3-yl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a colorless solution of 88.15 g 3-pentanol (1.0 mol) in 150 ml pyridine were added under stirring at 0° C. 126.0 g methanesulfonyl chloride (1.1 mol) over 1 h. After warming up (15 min.) and stirring at room temperature for 1 h, 50 ml deionized water were added all at once and stirring at room temperature was continued for 1 h. The reaction mixture was diluted with 500 ml ethyl acetate and washed with 800 ml 1N HCl and 250 ml 10% brine. Both aqueous layers were extracted sequentially with 250 ml ethyl acetate. After drying the combined organic layers over ca. 20 g Na2SO4, the solvent was removed on the rotary evaporator (50° C./≧1 mbar) affording 154.4 g (92.9%) yellow, oily title product, which could be used in the next step without purification.

Provenance & Evidence