Triethylamine → (Tetrahydrofuran-3-yl)methyl methanesulfonate

Participants

Reaction Steps

To a cooled (0° C.) solution of (tetrahydrofuran-3-yl)methanol (3.0 mL) and triethylamine (5.7 mL) in dichloromethane (30 mL) is added methanesulfonyl chloride (3.1 mL). The mixture is stirred for 12 hours at room temperature. After cooling to 0° C. triethylamine (1.3 mL) and methanesulfonyl chloride (0.7 mL) are added and the mixture is stirred for 12 hours at room temperature. The mixture is partitioned between dichloromethane and saturated aqueous NaHCO3 solution and stirred vigorously for 30 minutes. The organic phase is separated, washed with brine and dried (MgSO4). The solvent is evaporated to give the title compound. Yield: 5.6 g; TLC: rf=0.35 (silicagel, cyclohexane/ethyl acetate 1:1); Mass spectrum (ESI+): m/z=181 [M+H]+.

Provenance & Evidence