反应详情

温度

18 °C

To a stirred solution of (1R)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propan-1-ol (compound 6c, 50 g, 245 mmol), triphenylphosphine (195 g, 743 mmol), 4-nitrobenzoic acid (124 g, 743 mmol) in THF (1200 mL) was added diethyl azodicarboxylate (130 g, 743 mmol) dropwise at 0° C. under N2. After being stirred at 18° C. for 10 hours, the mixture was quenched by addition of saturated NaHCO3 solution and extracted with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether) to afford 61 g of [(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propyl] 4-nitrobenzoate (compound 6d) as a slight yellow solid.

1. customthe mixture was quenched by addition of saturated NaHCO3 solution
2. extractionextracted with EtOAc
3. dry with materialdried over Na2SO4
4. concentrationconcentrated in vacuo
5. customThe residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether)