反应详情

0.682 g of tert-butyl diethylphosphonoacetate (2.7 mmol, 1.1 eq.) is placed in 5 mL of DMF at 4° C. with stirring, 0.065 g of sodium hydride (2.7 mmol, 1.1 eq.) is added. After stirring for 1 hour, 0.64 g of ethyl trans-4-(4-formylcyclohexyl)benzoate (2.46 mmol, 1 eq.) dissolved in 5 mL of DMF is added dropwise. After stirring for 18 hours, 10% potassium hydrogen sulfate solution is added. The reaction medium is extracted twice with ethyl acetate. The organic phases are combined, washed twice with water, washed with brine, dried over sodium sulfate and evaporated. The residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 10% to 20%. 0.71 g of ethyl trans-4-[4-((E)-2-tert-butoxycarbonylvinyl)cyclohexyl]benzoate is obtained.

1. stirringAfter stirring for 1 hour
2. additionis added dropwise
3. stirringAfter stirring for 18 hours
4. extractionThe reaction medium is extracted twice with ethyl acetate
5. washwashed twice with water
6. washwashed with brine
7. dry with materialdried over sodium sulfate
8. customevaporated
9. customThe residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 10% to 20%