Ethyl bromoacetate → 3-Cyano-3-(3,4-dimethylphenyl)pentanedioic acid diethyl ester

HRID 343533

反応式

HRID 343533 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[CH3:8].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCCC1.C(OCC)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][C:9]([C:10]#[N:11])([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:28]

参加物

6

反応物 3

HCID 7748Ethyl bromoacetateHCID 764012-(3,4-Dimethylphenyl)acetonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

生成物 1

HCID 538454283-Cyano-3-(3,4-dimethylphenyl)pentanedioic acid diethyl ester

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

Combine 3,4-dimethylphenylacetonitrile (50.0 mmol) and tetrahydrofuran (140 mL). Cool to about 5° C. Add dropwise a solution of sodium bis(trimethylsilyl)amide (800 mL, 1M in tetrahydrofuran, 800 mmol). When the addition is complete, warm the reaction mixture to ambient temperature and allow to stir for 1 hour. Transfer the above solution via cannula into a cooled (-8° C.) solution of ethyl bromoacetate (84.5 mL, 762 mmol) in tetrahydrofuran (500 mL) at such a rate that the temperature of the reaction mixture does not rise above 20° C. Allow to stir at ambient temperature. After 18 hours, dilute with diethyl ether (1.5 L) and extract with saturated aqueous solution of ammonium chloride, then water, and then saturated aqueous solution of sodium chloride. Dry the organic layer over MgSO4, filter, and concentrate invacuo to give the title compound.

後処理

  1. additionWhen the addition
  2. temperaturewarm the reaction mixture to ambient temperature
  3. customdoes not rise above 20° C
  4. stirringto stir at ambient temperature
  5. waitAfter 18 hours
  6. extractionextract with saturated aqueous solution of ammonium chloride
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate invacuo

出典と根拠

ORDレコード
ord-130399e8c95d4e54a6ab3f2ada24a2e8
出典データセット
uspto-grants-1999_01
特許番号
US05861417

関連ノート

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