반응 #430257
ord-eb7d87f018034d5b9c825d0de2dc3539
반응 방정식
반응 조건
후처리
- 1온도The reaction was heated
- 2온도to reflux for 15 minutes
- 3온도cooled
- 4온도to reflux for 30 minutes
- 5추출The aqueous phase was extracted with ethyl acetate (2×700 mL)
- 6세척The combined organics were washed with brine
- 7건조dried over MgSO4
- 8여과filtered
- 9농축concentrated in vacuo
- 10기타yielding a brown oil
- 11건조dried with MgSO4, gravity
- 12여과filtered
- 13기타purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant
- 14농축The material was concentrated in vacuo
- 15기타crystallized from hexane/ethyl acetate
- 16기타The solid was isolated by filtration and air
- 17기타dried
실험 절차
Thionyl chloride (25 mL, 0.34 mol) was added dropwise to ethanol (540 mL). The reaction was heated to reflux for 15 minutes and cooled. The solution was treated with 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one from Step 1 (20.0 g, 72.64 mmol) and acetonylacetone (12.8 mL, 108.96 mmol), and reheated to reflux for 30 minutes. After cooling to room temperature, the solution was poured into rapidly stirred saturated aqueous Na2CO3 and ice (1500 mL). The aqueous phase was extracted with ethyl acetate (2×700 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo, yielding a brown oil. The oil was diluted with ethyl acetate (200 mL) and hexane (2000 mL), dried with MgSO4, gravity filtered, then purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant. The material was concentrated in vacuo and crystallized from hexane/ethyl acetate. The solid was isolated by filtration and air dried to afford 2,5-dimethyl-1-[[4-(2-oxo-2-phenylethyl)phenyl]sulfonyl]-1H-pyrrole (12.2 g, 49%) as a brown solid: mp 94.6°-98.8° C. 1H NMR (DMSO-d6 /300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 1H), 7.44 (d, J=8.26 Hz, 2H), 7.30 (br s, 2H), 4.52 (s, 2H). Mass spectrum: M+H obs. at m/z=354.