Acetone → 2-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)phenyl]propan-2-ol

HRID 1640135노트

반응식

HRID 1640135 반응식
Br[C:2]1[CH:3]=[C:4]([N:12]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]2[CH3:18])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C([Li])CCC.[CH3:24][C:25]([CH3:27])=[O:26].[NH4+].[Cl-]>C1COCC1.CCCCCC>[CH3:18][C:13]1[N:12]([C:4]2[CH:3]=[C:2]([C:25]([OH:26])([CH3:27])[CH3:24])[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=2)[C:16]([CH3:17])=[CH:15][CH:14]=1

참가 물질

7

반응물 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 589023221-[3-bromo-5-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrroleHCID 178418339Butyllithium

생성물 1

HCID 589022632-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)phenyl]propan-2-ol수율 49.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a solution of 1-[3-bromo-5-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole (4.98 g, 15.6 mmol) in THF (75 mL) at −78° C., was added a solution of 2.50M n-butyllithium in hexane dropwise. The reaction mixture was allowed to stir for 30 min and then acetone (1.49 mL, 20.4 mmol) was added dropwise. The reaction mixture was allowed to stir at −78° C. for 30 min, and then allowed to warm to rt. Saturated aq. NH4Cl was added and the mixture was extracted with EtOAc (3×). The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 2-[3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)phenyl]propan-2-ol (2.29 g, 49.2%). LCMS: (FA) ES+ 298.2.

후처리

  1. stirringto stir at −78° C. for 30 min
  2. extractionthe mixture was extracted with EtOAc (3×)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-f0cd2a4483274494981e5d8d97e79c2b
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110687B2

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