반응 #93685
ord-07dad5d65ceb4deab29eed308f16bb51
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시약
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후처리
- 1온도cooled to -20°
- 2기타the reaction approximately 80-85% complete
- 3기타the reaction
- 4기타the reaction
- 5기타now being 7°
- 6기타The phases are separated
- 7추출The aqueous portion is back-extracted with methylene chloride (10 ml)
- 8세척The organic extracts are washed with phosphate buffer (25 ml)
- 9추출back-extracted with methylene chloride (10 ml)
- 10기타dired over sodium sulfate overnight at 20°-25°
- 11여과This mixture is filtered
- 12농축the filtrate concentrated under reduced pressure to an oil, which
실험 절차
17α-Acetyl-17β-hydroxy-6,16-dimethyleneandrosta-4-en-3-one (Example 5, 8.0 g) is dissolved in methylene chloride (66 ml) and cooled to -20°. Trimethylamine (2.56 ml) at -20° and methylene chloride (5 ml) are mixed and the trimethylamine mixture transferred by syringe to the steroid solution. To the cold steroid solution was added phenylsulfonylchloride (1.0 equivalent) by a syringe pump over 1 hr. TLC shows the reaction approximately 80-85% complete. Phenylsulfonylchloride (0.25 equivalent) was added over approximately 10 min., TLC showing the reaction to be approximately 95% complete. Phenylsulfonylchloride (0.10 equivalent) was then added for a total of 1.35 equivalence, at which time TLC shows the reaction to be complete. Hydrochloric acid (10%, 40 ml) was added all at once, the temperature now being 7°, and the mixture stirred for about 10 min. The phases are separated. The aqueous portion is back-extracted with methylene chloride (10 ml). The organic extracts are washed with phosphate buffer (25 ml) and back-extracted with methylene chloride (10 ml). The organic extracts are combined, dired over sodium sulfate overnight at 20°-25°. This mixture is filtered and the filtrate concentrated under reduced pressure to an oil, which is the title compound.