Triethylamine → Oxan-4-yl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

4-Hydroxytetrahydropyran (4.86 g, 47.6 mmol) was dissolved in DCM (40 mL) and triethylamine (6.95 mL, 49.9 mmol). The reaction mixture was cooled to 0° C. and a solution of methanesulfonyl chloride (5.72 g, 49.9 mmol) in DCM (10 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 5 min and then allowed to warm to room temperature and stirred for 20 h. The solvents were removed in vacuo to give a white residue which was partitioned between EtOAc and H2O. The aq phase was extracted with EtOAc (2×100 mL). The organic layers were combined, dried (MgSO4) and the solvents were removed in vacuo to give tetrahydro-2H-pyran-4-yl methanesulfonate (8.53 g, 99%) as a colourless gum which solidified on standing.

Provenance & Evidence