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

HRID 2212270ノート

反応式

HRID 2212270 の反応式
[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]

参加物

7

反応物 3

HCID 7467P-ChloroacetophenoneHCID 7764Ethyl cyanoacetate2 回HCID 517165Ammonium Acetate

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒2 回HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 4′-chloroacetophenone (50 mmole), ethyl cyanoacetate (50 mmole), 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 mmole), 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/petroleum ether.

後処理

  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/petroleum ether

出典と根拠

ORDレコード
ord-ab00f3918425403abeb06bece96c1ea3
出典データセット
uspto-grants-2006_09
特許番号
US07101905B2

反応ノート

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