(Trifluoromethyl)trimethylsilane → 2,2,2-Trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanol

HRID 1988028ノート

反応式

HRID 1988028 の反応式
[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[F:14][C:15]([Si](C)(C)C)([F:17])[F:16]>C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:14][C:15]([F:17])([F:16])[CH:8]([C:7]1[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[OH:9]

参加物

5

反応物 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 104196252-(1H-imidazol-1-yl)benzaldehyde

生成物 1

HCID 667427962,2,2-Trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanol収率 93%

試薬・触媒・溶媒 2

HCID 2724141Tetrabutylammonium Fluoride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To 2-imidazol-1-yl-benzaldehyde (0.344 g, 2 mmol) in THF (8 ml) was added trifluoromethyltrimethyl silane (0.341 g, 2.4 mmol). The reaction mixture was cooled to 0-5° C. (ice water bath) and tetra-n-butyl ammonium fluoride (0.035 ml, 0.035 mmol, 1M in THF) was added. The ice bath was removed, and the mixture was stirred at room temperature for 6 hours. 2N HCl (5 ml) was added, and the reaction mixture was further stirred for 3 hours at room temperature. Solvent was removed on the rotavap under reduced pressure. Crude residue was dissolved in DCM (30 ml), washed with water (20 ml), brine (20 ml) and dried with sodium sulfate. The solvent was removed to give crude 2,2,2-trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanol (0.45 g, 93%), which was directly used in the next step.

後処理

  1. additionwas added
  2. customThe ice bath was removed
  3. addition2N HCl (5 ml) was added
  4. stirringthe reaction mixture was further stirred for 3 hours at room temperature
  5. customSolvent was removed on the rotavap under reduced pressure
  6. dissolutionCrude residue was dissolved in DCM (30 ml)
  7. washwashed with water (20 ml), brine (20 ml)
  8. dry with materialdried with sodium sulfate
  9. customThe solvent was removed

出典と根拠

ORDレコード
ord-ac048ef52dff46eb981859c6f77354f5
出典データセット
uspto-grants-2009_06
特許番号
US07553840B2

反応ノート

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