P-Chloroacetophenone → 3-(4-Chlorophenyl)-2-cyano-but-2-enoic acid ethyl ester

HRID 270179노트

반응식

HRID 270179 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[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:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:9])[CH3:18]

참가 물질

7

반응물 3

HCID 7467P-ChloroacetophenoneHCID 7764Ethyl cyanoacetate2회HCID 517165Ammonium Acetate

생성물 1

HCID 5337753-(4-Chlorophenyl)-2-cyano-but-2-enoic acid ethyl ester

시약·촉매·용매 3

HCID 176Acetic Acid용매2회HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4′-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 10 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 an additional 10 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-38a7e6a3425e4d6da384f450c1bb80b0
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449490B2

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