1,1'-Carbonyldiimidazole → N-methoxy-N-methyloxane-4-carboxamide

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Reaction Steps

Add 1,1′-carbonyldiimidazole (333.41 g, 1.2 eq) to a solution of tetrahydro-2H-pyran-4-carboxylic acid (223 g, 1.71 mol) in dichloromethane (2.23 L) portion wise over 15 minutes. Stir for two hours. Add N,O-dimethylhydroxylamine hydrochloride (183.86 g, 1.1 eq) portionwise and stir for three hours. Wash the organics with saturated aqueous ammonium chloride, then with saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate and concentrate in vacuo to give N-methoxy-N-methyl-tetrahydropyran-4-carboxamide (339 g, 114%) as crude material and use as such in next reaction. 1H NMR (300 MHz, DMSO-d6) δ 4.02 (m, 2H), 3.71 (s, 3H), 3.46 (m, 2H), 3.19 (s, 3H), 2.91 (m, 1H), 1.86 (m, 2H), 1.65 (m, 2H).

Provenance & Evidence