Methanesulfonyl chloride → Cyclopent-3-en-1-yl methanesulfonate

Participants

Reaction Steps

To a solution of 3-cyclopentene-1-ol (9.00 g, 107 mmol) in dry methylene chloride (150 mL) was added TEA (23.0 mL, 160 mmol) followed by DMAP (100 mg). To this solution was added methanesulfonyl chloride (14.72 g, 128 mmol) at 10-20° C. slowly over 15 minutes and stirred overnight at room temperature. To the reaction mixture was added aqueous saturated NaHCO3 (50 mL) and stirred for 15 minutes at room temperature. The organic layer was separated, washed with water, followed by brine and dried over NaSO4. It was filtered and concentrated to give the title compound as an oil that was used without purification in the next reaction. 1H NMR (300 MHz, CDCl3): δ=5.72 (s, 2H), 5.38 (mc, 1H), 3.00 (s, 3H), 2.81-2.61 (m, 4H).

Provenance & Evidence