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

HRID 344719

반응식

HRID 344719 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2e80f1fe8b8e49ef8601f4714a0385df
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05053408

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