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

HRID 1059164노트

반응식

HRID 1059164 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6299ccd2a5dd4a02b8b88c7f37764663
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518257B1

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