4-Toluenesulfonyl chloride → 2H-Pyran, 2-(5-hexenyloxy)tetrahydro-

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Reaction Steps

To a solution of 8.5 g 5-hexen-1-ol in 100 mL tetrahydrofuran is added 14 mL dihydropyran followed by 0.5 g p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 18 hours and then diluted with ether. The mixture is then washed with saturated aqueous sodium bicarbonate, dried, filtered and evaporated. The resulting oil is chromatographed over silica gel using hexane/ether (18:1) as eluent to give 6-(2-tetrahydropyranyloxy)-hex-1-ene; NMR (CDCl3): delta 5.85 (m,1H), 4.6 (brs,1H).

Provenance & Evidence