反应详情

温度

0 °C

To a stirring mixture consisting of lithium chloride (3.75 g, 88.5 mmol) and triethylamine (4.86 mL) in THF (350 mL) cooled to 0° C. and stirred for 5 minutes at that temperature was added a solution consisting of dimethyl 2-(2,3-dihydro-1H-inden-2-yl)-2-oxoethylphosphonate (8.61 g) in THF (100 mL). The reaction mixture was stirred for 5 minutes and a solution consisting of (Z)-isopropyl 7-((1R,2S,3S,5S)-3-fluoro-2-formyl-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (prepared in Step G, 10.31 g) in THF was added slowly. The reaction mixture was stirred as it was allowed to warm to room temperature overnight. The reaction mixture was subsequently acidified with 5% KHSO4, extracted with DCM, and the organic layers were washed twice with brine. After drying over sodium sulfate, filtration, and solvent removal under reduced pressure, the crude product was purified on silica gel. Elution with hexanes-ethyl acetate (9:1) afforded the title intermediate (13.4 g, 94%).

1. additionwas added a solution
2. stirringThe reaction mixture was stirred for 5 minutes
3. additionwas added slowly
4. stirringThe reaction mixture was stirred as it
5. temperatureto warm to room temperature overnight
6. extractionextracted with DCM
7. washthe organic layers were washed twice with brine
8. dry with materialAfter drying over sodium sulfate, filtration, and solvent removal under reduced pressure
9. customthe crude product was purified on silica gel
10. washElution with hexanes-ethyl acetate (9:1)