3,4-dihydro-2H-pyran → 2-(3-Iodomethyl-cyclopentyloxy)-tetrahydropyran

Participants

Reaction Conditions

Reaction Steps

A solution of 3-iodomethyl-cyclopentanol (7.71 g, 34.10 mmol) in methylene chloride (171 mL) was treated with 3,4-dihydro-2H-pyran (4.7 ml, 51.16 mmol) and pyridinium p-toluenesulfonate (857.1 mg, 3.41 mmol). The resulting reaction mixture was stirred at 25° C. for 24 h. The reaction mixture was then washed with a saturated aqueous sodium chloride solution (1×200 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 19/1 petroleum ether/diethyl ether) afforded 2-(3-iodomethyl-cyclopentyloxy)-tetrahydropyran (7.91 g, 75%) as a yellow oil: EI-HRMS m/e calcd for C11H19IO2 (M+) 310.0430, found 310.0433.

Provenance & Evidence