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

HRID 270163ノート

反応式

HRID 270163 の反応式
[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]

参加物

8

反応物 4

HCID 7410AcetophenoneHCID 7764Ethyl cyanoacetate2 回HCID 517165Ammonium Acetate2 回HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2cbe06d157694f0eb7719a4485f3438d
出典データセット
uspto-grants-2008_11
特許番号
US07449490B2

反応ノート

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