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

HRID 1640135ノート

反応式

HRID 1640135 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f0cd2a4483274494981e5d8d97e79c2b
出典データセット
uspto-grants-2012_02
特許番号
US08110687B2

反応ノート

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