Ammonium Chloride → 1-(4'-fluoro[1,1'-biphenyl]-3-yl)-1-(1-trityl-1H-imidazol-4-yl)-1-ethanol

HRID 1059164ノート

反応式

HRID 1059164 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[C:20]([N:39]1[CH:43]=[C:42]([C:44](=[O:46])[CH3:45])[N:41]=[CH:40]1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>C1COCC1.CCCCCC>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:44]([C:42]3[N:41]=[CH:40][N:39]([C:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:43]=3)([OH:46])[CH3:45])[CH:3]=2)=[CH:9][CH:10]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 27569773-Bromo-4'-fluorobiphenylHCID 104280901-(1-trityl-1H-imidazol-4-yl)ethanoneHCID 178418339Butyllithium

生成物 1

HCID 186685141-(4'-fluoro[1,1'-biphenyl]-3-yl)-1-(1-trityl-1H-imidazol-4-yl)-1-ethanol収率 55.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

To a solution of 3-bromo-4′-fluoro-1,1′-biphenyl (1.50 g) in THF (20 ml) was added dropwise a solution (1.6 M; 3.73 ml) of n-butyllithium in hexane at −78° C., and the mixture was stirred for 20 min. A solution of 1-(1-trityl-1H-imidazol-4-yl)-1-ethanone (1.91 g) in THF (25 ml) was added dropwise at −78° C., and the mixture was stirred at −78° C. for 1 h, at −35 to −10° C. for 1 h and at 0° C. for 1 h. Saturated aqueous ammonium chloride solution was added to the reaction mixture and the mixture was extracted with ethyl acetate, washed with saturated brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by column chomatography (eluent, hexane:ethyl acetate=3:1→1:1) and recrystallized from ethyl acetate-hexane to give the title compound (1.57 g) as colorless prism crystals.

後処理

  1. stirringthe mixture was stirred at −78° C. for 1 h, at −35 to −10° C. for 1 h and at 0° C. for 1 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chomatography (eluent, hexane:ethyl acetate=3:1→1:1)
  7. customrecrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-6299ccd2a5dd4a02b8b88c7f37764663
出典データセット
uspto-grants-2003_02
特許番号
US06518257B1

反応ノート

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