4-Toluenesulfonyl chloride → (S)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of (R)-tetrahydrofuran-3-ol (3 g, 34.1 mmole) and Et3N (6.9 g, 68.2 mmole) in DCM (40 mL) at 0° C. was added 4-methylbenzene-1-sulfonyl chloride (7.2 g, 37.5 mmole). The mixture was stirred at room temperature for 8 h. The mixture was washed with water, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 15% ethyl acetate in hexane) to give the title compound (6.6 g, 80% yield). MS (ESI) m/z: Calc. 242.1 (M+). Found: 243.1 (M++1).

Provenance & Evidence