Acetophenone → Ethyl 2-cyano-3-phenyl-2-butenoate

HRID 270163노트

반응식

HRID 270163 반응식
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.C(O)(=O)C.C1C=CC=CC=1>[CH2:16]([O:15][C:13](=[O:14])[C:12]([C:10]#[N:11])=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2])[CH3:17]

참가 물질

8

반응물 4

HCID 7410AcetophenoneHCID 7764Ethyl cyanoacetate2회HCID 517165Ammonium Acetate2회HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

생성물 1

HCID 29024Ethyl 2-cyano-3-phenyl-2-butenoate

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of acetophenone (50 mmol), ethyl cyanoacetate (50 mmol), 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 mL) 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 dried (Na2S04). 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, affording an oil that solidified on standing at room temperature.

후처리

  1. temperatureto reflux in a Dean-Stark apparatus
  2. waitAfter an additional 10 hours
  3. washwashed with water (240 mL), brine (40 mL)
  4. customdried (Na2S04)
  5. filtrationAfter filtering
  6. concentrationthe extract was concentrated in vacuo
  7. additionthe desired product, as a mixture of E and Z-isomers
  8. customwas isolated by column chromatography on silica gel
  9. washeluting with 5% ethyl acetate in petroleum ether
  10. customaffording an oil that
  11. customon standing at room temperature

출처 및 근거

ORD 기록
ord-2cbe06d157694f0eb7719a4485f3438d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449490B2

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