反应详情

To a suspension of 60% sodium hydride (366 mg) and anhydrous tetrahydrofuran (50 ml) under ice-cooling was added diethyl 2-oxopropylphosphonate (1.78 g). The mixture was stirred for 15 minutes and then a solution of t-butyl trans-4-formylcyclohexylcarbamate (1.38 g) in anhydrous tetrahydrofuran (10 ml) was added thereto under the same condition. The mixture was stirred at room temperature for 3 hours, and then saturated aqueous ammonium chloride was added to the reaction mixture. The mixture was extracted with toluene, 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 1.32 g of t-butyl trans-4-[(E)-3-oxo-1-butenyl]cyclohexylcarbamate.

1. temperaturecooling
2. stirringThe mixture was stirred at room temperature for 3 hours
3. extractionThe mixture was extracted with toluene
4. washthe organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. customthe solvent was removed in vacuo
7. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)