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

HRID 323228

반응식

HRID 323228 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
5 °C

실험 절차

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, 1 M 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 in vacuo to give the title compound.

후처리

  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 in vacuo

출처 및 근거

ORD 기록
ord-756a01bc0c604bff8800e36c04815fab
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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