2-Bromopropane → 3-Methyl-2-(3,4,5-trimethoxyphenyl)butanenitrile

HRID 344719

反応式

HRID 344719 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]#[N:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[H-].[Na+].Br[CH:19]([CH3:21])[CH3:20].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:20][CH:19]([CH3:21])[CH:13]([C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:14]#[N:15]

参加物

6

反応物 4

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 258873,4,5-TrimethoxyphenylacetonitrileHCID 516892Sodium Bicarbonate

生成物 1

HCID 46615743-Methyl-2-(3,4,5-trimethoxyphenyl)butanenitrile収率 54.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

With stirring under ice cooling, 20.25 g (97.7 mmols) of 3,4,5-trimethoxyphenylacetonitrile was added by small portions to 50 ml of a solution of 2.45 g (102.1 mmols) of sodium hydride in dimethylformamide. The solution was dropwise added to 100 ml of a solution of 12.45 g (101.2 mmols) of 2-bromopropane in dimethylformamide with stirring under ice cooling. The mixture was stirred under ice cooling for further 3 hours. After the reaction, an aqueous saturated sodium bicarbonate solution was added to the mixture followed by extraction of the solution with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate =4/1) to afford 13.2 g (yield: 54%) of 3-methyl-2-(3,4,5-trimethoxyphenyl)butyronitrile.

後処理

  1. stirringwith stirring under ice cooling
  2. stirringThe mixture was stirred under ice cooling for further 3 hours
  3. customAfter the reaction
  4. extractionfollowed by extraction of the solution with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate =4/1)

出典と根拠

ORDレコード
ord-2e80f1fe8b8e49ef8601f4714a0385df
出典データセット
uspto-grants-1991_10
特許番号
US05053408

関連ノート

読み込み中…