反应详情

In a three-necked round bottom flask, sodium hydride 60% (1.04 g, 26.0 mmol) was suspended in dimethoxyethane (15 mL) at 0° C. Ethyl[bis(2,2,2-trifluoroethoxy)phosphinyl]acetate (8.63 g, 26.0 mmol) was added and the mixture was stirred at room temperature for 15 minutes. A solution of 1-{3-(3-methoxypropoxy)-4-[(triisopropylsilyl)oxy]phenyl}ethanone (6.60 g, 17.3 mmol) and dimethoxyethane (20 mL) was added and the mixture was brought to reflux and stirred for 1 hr. The reaction mixture was hydrolyzed with saturated aqueous ammonium chloride (80 mL). The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2) to yield 7.5 g (81%) of the desired product as a colorless oil of a mixture of E and Z isomers.

1. temperatureto reflux
2. stirringstirred for 1 hr
3. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2)
9. customto yield