Hydrochloric Acid → 4-(iodomethyl)tetrahydro-2H-pyran-4-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of trimethylsulfoxonium chloride (3.08 g, 23.73 mmol) and 2 N aq. sodium hydroxide (11.33 mL, 22.65 mmol) in tetrahydrofuran (13 mL) was heated at 50° C. for 1 h. 2.16 g (21.57 mmol) of tetrahydro-4H-pyran-4-one was added to the mixture and the mixture was stirred at 50° C. for 30 min. After cooling to room temperature, 3.56 g (23.73 mmol) of sodium iodide and 2 N hydrochloric acid (10.8 mL, 21.57 mmol) were added to the mixture. After being stirred at room temperature for 19 h, ethyl acetate was added to the mixture. The mixture was extracted with ethyl acetate three times and the extracts were combined. The extracts were dried over sodium sulfate and concentrated in vacuo to afford a beige solid. The residual solid was recrystallized from acetonitrile to afford 3.13 g (55%) of the title compound.

Provenance & Evidence