4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid tetrahydro-furan-3-ylmethyl ester

Participants

Reaction Steps

To a solution of tetrahydro-3-furanmethanol (6.2 g, 60.8 mmol) in 60 mL tetrahydrofuran was added p-toluenesulfonyl chloride (11.6 g, 60.9 mmol) in one portion, followed by the drop-wise addition of triethylamine (9.2 mL, 66.4 mol) over 10 min. The resulting mixture was stirred at reflux for 16 h and then treated with triethylamine (1.6 mL, 11.5 mmol). Heating was continued for an additional 18 h. The cooled mixture was diluted with diethyl ether, washed with water and brine, and dried over MgSO4. The mixture was then filtered and concentrated under reduced pressure. The resulting residue was placed on a column of silica gel (30 g) and eluted with 5% to 80% ethyl acetate in hexanes to give 11.0 g (72%) of the title compound as an orange oil.

Provenance & Evidence