1-Diethoxyphosphorylpropan-2-one → HCID 178467819, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium hydride (793 mg) and anhydrous tetrahydrofuran (80 ml) under ice-cooling was added diethyl 2-oxopropylphosphonate (3.85 g). The mixture was stirred for 15 minutes and then a solution of t-butyl trans-4-formylcyclohexylcarbamate (3.00 g) in anhydrous tetrahydrofuran (30 ml) was added thereto. The mixture was warmed to 25° C. and stirred for 3 hours. To the reaction mixture was added saturated aqueous ammonium chloride, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 3.46 g of t-butyl trans-4-[(E)-3-oxo-1-butenyl]cyclohexylcarbamate.

Provenance & Evidence