Diethyl Carbonate → HCID 89894058, compound

Participants

Reaction Conditions

Reaction Steps

(R)-2-(Benzyloxymethyl)oxirane (2.5 g, 15.23 mmol) was added dropwise to hydrazine mono-hydrate (4.67 g, 91 mmol), previously heated at 95° C., under vigorous stirring. The mixture was refluxed for 30 min. The excess of hydrazine hydrate was evaporated under vacuum for 3 h, at 53° C. and then at r.t., under vigorous magnetic stirring, for 18 h. A sticky colourless oil was obtained. The crude was dissolved in dry MeOH (5 mL) and a solution of sodium methoxide 0.5M in methanol (4.6 mL, 2.284 mmol), then diethyl carbonate (2.16 g, 18.27 mmol) were added dropwise. The mixture was refluxed for 6 h. The solvent was evaporated and the crude purified by flash silica-gel chromatography (DCM/MeOH=75:1) affording the title compound as a yellow oil that solidified on standing into a white solid (2.232 g, 10.04 mmol). Yield=66%.

Provenance & Evidence