Ethyl cyanoacetate → 2-Cyano-3-(3-methylphenyl)-but-2-enoic acid ethyl ester

HRID 270166

반응식

HRID 270166 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)[CH3:9])[CH3:18]

참가 물질

7

반응물 3

HCID 7764Ethyl cyanoacetate2회HCID 114553-MethylacetophenoneHCID 517165Ammonium Acetate

생성물 1

HCID 2977862-Cyano-3-(3-methylphenyl)-but-2-enoic acid ethyl ester

시약·촉매·용매 3

HCID 176Acetic Acid용매2회HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 3′-methylacetophenone (50 mmol), ethyl cyanoacetate (50 mmol), 25 acetic acid (1.14 mL) ammonium acetate (400 mg), and benzene (50 mL) was 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 was cooled to room temperature, diluted with ethyl acetate (30 mL), washed with water (240 mL), brine (40 mL), and 30 dried (Na2SO4). After filtering, the extract was concentrated in vacuo and the desired product, as a mixture of E and Z-isomers, was isolated by column chromatography on silica gel, eluting with 5% ethyl acetate in petroleum ether. The purified oil solidified on standing at room temperature.

후처리

  1. temperaturewas heated
  2. temperatureto reflux in a Dean-Stark apparatus
  3. waitAfter an additional 10 hours
  4. washwashed with water (240 mL), brine (40 mL), and 30
  5. dry with materialdried (Na2SO4)
  6. filtrationAfter filtering
  7. concentrationthe extract was concentrated in vacuo
  8. additionthe desired product, as a mixture of E and Z-isomers
  9. customwas isolated by column chromatography on silica gel
  10. washeluting with 5% ethyl acetate in petroleum ether
  11. customon standing at room temperature

출처 및 근거

ORD 기록
ord-f2ec646ed84c45559c6caa01c5677804
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449490B2

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