Water → 4-(3-Butyl-4-cyano-2-methylpyrrole-1-yl)benzoic acid ethyl ester

HRID 570834ノート

反応式

HRID 570834 の反応式
[CH2:1]([C:5]1[C:6]([C:11]#[N:12])=[CH:7][NH:8][C:9]=1[CH3:10])[CH2:2][CH2:3][CH3:4].[CH2:13]([O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=1)[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:13]([O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][C:20]([N:8]2[CH:7]=[C:6]([C:11]#[N:12])[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:9]2[CH3:10])=[CH:19][CH:18]=1)[CH3:14]

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 59478041HCID 59478041、化合物

生成物 1

HCID 594780574-(3-Butyl-4-cyano-2-methylpyrrole-1-yl)benzoic acid ethyl ester収率 20.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A suspension of 4-butyl-5-methyl-1H-pyrrole-3-carbonitrile (0.081 g), 4-fluoro-benzoic acid ethyl ester (0.10 g) and cesium carbonate (0.21 g) in N,N-dimethylformamide (3 mL) was stirred at 70° C. overnight. This reaction mixture was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/6) to give the title compound (0.032 g).

後処理

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/6)

出典と根拠

ORDレコード
ord-3e1bea7c31ef45f1b3828ba6ae3d7997
出典データセット
uspto-grants-2015_05
特許番号
US09023882B2

反応ノート

読み込み中…