Tetrahydropyran-2-methanol → Oxan-2-ylmethyl methanesulfonate

Participants

Reaction Steps

In 200 ml of toluene, 23.2 g (200 mmol) of tetrahydropyran-2-ylmethanol were admixed with 27.5 g (240 mmol) of methanesulfonyl chloride. At 10° C., 24.3 g (240 mmol) of triethylamine were then added dropwise, and stirring was continued for 2 hours at room temperature. 200 ml of methyl tert-butyl ether and 200 ml of water were then added to the mixture and the organic phase was separated off, washed with 200 ml of water and dried. Removal of the solvent under reduced presure gave 33.7 g (87% of theory) of a clear oil. (1H-NMR (CDCl3; δ in ppm): 4.20 (d,2H); 4.05 (dd,1H); 3.60 (m,1H); 3.45 (m,1H); 3.1 (s,3H); 1.95 (m,1H); 1.45 (m,5H))

Provenance & Evidence