Ethyl cyanoacetate → Ethyl 3-(2-chlorophenyl)-2-cyanobut-2-enoate

HRID 270176

반응식

HRID 270176 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH3:9].[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.C(O)(=O)C.C1C=CC=CC=1>[CH2:17]([O:16][C:14](=[O:15])[C:13]([C:11]#[N:12])=[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:9])[CH3:18]

참가 물질

7

반응물 3

HCID 7764Ethyl cyanoacetate2회HCID 72864Ethanone, 1-(2-chlorophenyl)-HCID 517165Ammonium Acetate

생성물 1

HCID 67073569Ethyl 3-(2-chlorophenyl)-2-cyanobut-2-enoate

시약·촉매·용매 3

HCID 176Acetic Acid용매2회HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2′-chloroacetophenone (50 mmol), ethyl cyanoacetate (50 mmol), acetic acid (1.14 mL) ammonium acetate (400 mg), and benzene (50 mL) is heated to reflux in a Dean-Stark apparatus. After approximately hours, additional ethyl cyanoacetate (50 mmol), acetic acid (1.14 mL), and ammonium acetate (400 mg) are added. After an additional 10 hours, the reaction is cooled to room temperature, diluted with ethyl acetate (30 mL), washed with water (240 mL), brine (40 mL), and dried (Na2SO4). After filtering, the extract is concentrated in vacuo and the desired product, as a mixture of E and Z-isomers, is isolated by column chromatography on silica gel, eluting with 5% ethyl acetate in petroleum ether.

후처리

  1. temperatureis heated
  2. temperatureto reflux in a Dean-Stark apparatus
  3. waitAfter approximately hours
  4. washwashed with water (240 mL), brine (40 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationAfter filtering
  7. concentrationthe extract is concentrated in vacuo
  8. additionthe desired product, as a mixture of E and Z-isomers
  9. customis isolated by column chromatography on silica gel
  10. washeluting with 5% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-fd54da5602114e94950de7957523fde0
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449490B2

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