반응 #217614
ord-6c7576c8889e4184bf20253481c4a9c9
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반응물
시약
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후처리
- 1기타the layers separated
- 2추출The aqueous layer was then re-extracted with dichloromethane (100 ml)
- 3세척the combined organic fractions washed with saturated aqueous sodium hydrogen carbonate (200 ml)
- 4기타The layers were separated
- 5추출the aqueous re-extracted with dichloromethane (100 ml)
- 6건조dried over sodium sulfate
- 7여과filtered
- 8기타evaporated
- 9workup.DISSOLUTIONThe resulting solid was then dissolved in dichloromethane (40 ml)
- 10온도with warming
- 11온도to cool
- 12기타purified by chromatography on silica gel eluting with 10-15% diethyl ether/hexane
실험 절차
To a stirred solution of 4-[(phenyhnethyl)oxy]benzenesulfonyl chloride (D48) (13.77 g, 48.70 mmol) in dichloromethane (265 ml) was added triethylamine (9.16 ml, 65.75 mmol) under argon and the mixture cooled to −15° C. A solution of pentafluorophenol (9.86 g, 53.57 mmol) in dichloromethane (20 ml+20 ml wash) was then added quickly and the reaction allowed to wami slowly to room temperature over 1.75 h. Hydrochloric acid (2M, 250 ml) was then added and the mixture stirred for 20-30 min and the layers separated. The aqueous layer was then re-extracted with dichloromethane (100 ml) and the combined organic fractions washed with saturated aqueous sodium hydrogen carbonate (200 ml). The layers were separated and the aqueous re-extracted with dichloromethane (100 ml). All the dichloromethane layers were combined and dried over sodium sulfate, filtered and evaporated. The resulting solid was then dissolved in dichloromethane (40 ml) with warming, and allowed to cool and then purified by chromatography on silica gel eluting with 10-15% diethyl ether/hexane to afford the title compound (D49). 1H-NMR (d6-DMSO) d 7.97-7.94 (2H, m), 7.50-7.31 (7H, m), 5.29 (2H, s).