Ethyl benzoylformate → HCID 54747357, compound

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Reaction Steps

Ethyl 3-[2-[2-(ethyloxy)-2-oxo-l-phenylethylidene]-1-(phenylmethyl)hydrazino]-3-oxopropanoate. A mixture of ethyl oxo(phenyl)acetate (0.315 g, 1.77 mmol), benzylhydrazine dihydrochloride (0.334 g, 1.71 mmol), diisopropylethylamine (0.596 mL, 3.42 mmol), dichloromethane (10 mL) and excess magnesium sulfate was stirred for 18 h, then filtered through a plug of silica gel and the cake washed with 50% ethyl acetate/hexane. The solvent was removed under reduced pressure and the crude hydrazone dissolved in tetrahydrofuran (5 mL) and placed under nitrogen. 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.212 mL, 1.42 mmol) was added, followed by ethyl 3-chloro-3-oxopropionate (0.182 mL, 1.42 mmol) dropwise. The mixture was stirred at room temperature for 2 h, then poured into water (50 mL) and extracted with ethyl acetate. The extracts were dried (MgSO4), evaporated under reduced pressure and the residue chromatographed (silica gel, 10-50% ethyl acetate/hexane) to give the title compound (0.117 g) as a gum, sufficiently pure to use in the next reaction. LCMS (ES+) m/z 397 (MH+).

Provenance & Evidence