Hydrochloric Acid → [2-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol

HRID 554294노트

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HRID 554294 반응식
[Cl:1][C:2]1[N:3]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7](OCC)=[O:8].[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][C:6]=1[CH2:7][OH:8]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 66924662Ethyl 2-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate

생성물 1

HCID 66924752[2-Chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol수율 78%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

A solution (30 mL) of ethyl 2-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate (1.27 g) in tetrahydrofuran was cooled to −70° C., a 1.5 mol/L solution (7.6 mL) of diisobutylaluminum hydride in toluene was added dropwise by small portions. The mixture was further stirred at −70° C. for 1 hr, 1 mol/l hydrochloric acid (20 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3→1:1) to give the title compound as pale-red crystals (yield 882 mg, 78%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3→1:1)

출처 및 근거

ORD 기록
ord-0b5fb0927674481cb3d251571543d639
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048909B2

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