Ethanol → Ethyl 5-(hydroxymethyl)-4,5-dihydro-1,2-oxazole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of allylic alcohol (0.650 mL; 9.35 mmol) and ethyl 2-nitroacetate (2.65 mL; 23.37 mmol) in ethanol (12 mL) in an Ace pressure tube was added 1,4-diazobicyclo[2.2.2]octane (DABCO, 0.189 g; 1.64 mmol). The tube was heated at 80° C. for 48 h. The mixture was evaporated. The flash chromatography on silica gel (eluent: 0 to 6% of methanol in dichloromethane) of the residue provided 1.51 g (93%) of ethyl 5-(hydroxymethyl)-4,5-dihydroisoxazole-3-carboxylate as an oil.

Provenance & Evidence