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

HRID 1694787ノート

反応式

HRID 1694787 の反応式
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

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 58951927HCID 58951927、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)+.).

後処理

  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)

出典と根拠

ORDレコード
ord-1cc8a51e2df0438ab325748bc1123a2a
出典データセット
uspto-grants-2012_04
特許番号
US08158668B2

反応ノート

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