반응 #42654

반응 방정식

boron trifluoride etherate

hexane ethyl acetate dichloromethane methanol

(11β,16β)-21-(acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamate

boron trifluoride etherate

→

(11β,16β)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl ethylcarbamate

용매

acetonitrile

반응 조건

후처리

1. 1
   workup.STIRRINGThe solution was stirred at room temperature for 15 hours more
2. 2
   기타was then partitioned between ethyl acetate and water
3. 3
   세척The organic layer was washed with water (twice) and brine
4. 4
   건조dried over Na2SO4
5. 5
   여과Filtration and evaporation under vacuum
6. 6
   기타gave a pale yellow oil

실험 절차

To a solution of (11β,16β)-21-(acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamate (138 mg, 0.239 mmol) in 2.5 mL of acetonitrile was added boron trifluoride etherate (0.12 mL, 0.96 mmol). After stirring at room temperature for 5 hours, additional boron trifluoride etherate (0.060 mL, 0.47 mmol) was added. The solution was stirred at room temperature for 15 hours more and was then partitioned between ethyl acetate and water. The organic layer was washed with water (twice) and brine and dried over Na2SO4. Filtration and evaporation under vacuum gave a pale yellow oil. Chromatography on silica gel eluting with hexane/ethyl acetate/dichloromethane/methanol (5:2:2:1) gave (11β,16β)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl ethylcarbamate as a white film.

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