Diethyl Ether → 1-(Tetrahydro-2H-pyran-4-yl)ethanone

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Reaction Steps

Add 3 M methyl magnesium bromide in diethyl ether (1.14 L, 2.0 eq) to a solution of N-methoxy-N-methyl-tetrahydropyran-4-carboxamide (296 g, 1.71 mol) in tetrahydrofuran (2.96 L) over one hour at 0° C. Stir for an additional two hours, then pour the contents into a mixture of ice/water. Extract with methyl tert-butyl ether. Dry the organics over anhydrous magnesium sulfate and concentrate in vacuo to give 1-(tetrahydro-pyran-4-yl)-ethanone (105 g, 48%). 1H NMR (300 MHz, DMSO-d6) δ 3.98 (m, 2H), 3.42 (m, 2H), 2.52 (m, 1H), 2.15 (s, 3H), 1.74 (m, 4H).

Provenance & Evidence