Hydrochloric Acid → (1H-Imidazol-4-yl)(phenyl)methanol

HRID 1694787노트

반응식

HRID 1694787 반응식
Cl.CN(C)S([N:7]1[CH:11]=[C:10]([CH:12]([OH:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=[C:8]1[Si](C(C)(C)C)(C)C)(=O)=O>CO>[OH:19][CH:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:10]1[NH:9][CH:8]=[N:7][CH:11]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 58951927HCID 58951927, 화합물

생성물 1

HCID 15082952(1H-Imidazol-4-yl)(phenyl)methanol수율 28.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A gentle stream of HCl gas was bubbled through a refluxing solution of 2-(tert-butyl-dimethyl-silanyl)-4-(hydroxy-phenyl-methyl)-imidazole-1-sulfonic acid dimethylamide (0.2 g, 0.51 mmol) in methanol (5 ml) for 1 hour. The solvent was evaporated and sodium hydroxide solution was added. The mixture was extracted with dichloromethane (2 times). The combined organic layers are dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, dichloromethane/methanol/aqueous conc. ammonia=90:10:1) to yield 25 mg (26%) of rac-5-(hydroxy-phenyl-methyl)-1H-imidazole, MS (EI): 174.1 ((M+.) and 5 mg (5%) of rac-5-(methoxy-phenyl-methyl)-1H-imidazole as colourless oil: MS (ISP): 189.1 ((M+H)+.).

후처리

  1. customThe solvent was evaporated
  2. additionsodium hydroxide solution was added
  3. extractionThe mixture was extracted with dichloromethane (2 times)
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica gel, dichloromethane/methanol/aqueous conc. ammonia=90:10:1)

출처 및 근거

ORD 기록
ord-1cc8a51e2df0438ab325748bc1123a2a
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158668B2

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