Water → Ethyl 4,4,4-trifluoro-3-methyl-2-(4-{[2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl]methyl}phenyl)butanoate

HRID 877251ノート

反応式

HRID 877251 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6](=[O:9])[NH:7][CH:8]=1.[H-].[Na+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH:28]([CH3:33])[C:29]([F:32])([F:31])[F:30])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:17]=1.O>CN(C=O)C>[F:30][C:29]([F:31])([F:32])[CH:28]([CH3:33])[CH:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:7]2[CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=[CH:5][C:6]2=[O:9])=[CH:21][CH:20]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1474432-Hydroxy-5-(trifluoromethyl)pyridineHCID 58136537Ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate

生成物 1

HCID 58136589Ethyl 4,4,4-trifluoro-3-methyl-2-(4-{[2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl]methyl}phenyl)butanoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1.80 g (11.04 mmol) of 5-(trifluoromethyl)pyridin-2(1H)-one were initially charged in 2.5 ml of DMF, and 0.44 g (11.04 mmol, 60% pure) of sodium hydride was added. The mixture was stirred for 30 min, and 3.0 g (8.49 mmol) of ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate were then added. After a further 2 h at RT, water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 4:1). This gave 2.89 g (78.2% of theory) of the target compound.

後処理

  1. waitAfter a further 2 h at RT
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 4:1)

出典と根拠

ORDレコード
ord-56f42e2c4f4d4139808532374dc05b4e
出典データセット
uspto-grants-2015_03
特許番号
US08987256B2

反応ノート

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