3,4-dihydro-2H-pyran → 2-Methyl-3-butyn-2-yl 2-tetrahydropyranyl ether

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Reaction Steps

To a solution of 2-methyl-3-butyn-2-ol (17.0 g, 202.1 mmol) in dichloromethane (200 mL) cooled to 0° C. was added 2,3-dihydropyran (22.0 mL, 258.4 mmol), followed by para-toluenesulfonic acid (10 mg, 0.05 mmol). The mixture was allowed to slowly warm to room temperature over 3 h, then washed with a saturated aqueous solution of sodium bicarbonate, followed by brine, then dried (sodium sulfate), and concentrated to provide 34.0 g (97%) of 2-(1,1-dimethyl-prop-2-ynyloxy)-tetrahydropyran as a clear oil.

Provenance & Evidence