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

HRID 2212257

反応式

HRID 2212257 の反応式
[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]

参加物

7

反応物 3

HCID 7764Ethyl cyanoacetate2 回HCID 114553-MethylacetophenoneHCID 517165Ammonium Acetate

生成物 1

HCID 2977862-Cyano-3-(3-methylphenyl)-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 3′-methylacetophenone (50 mmole), ethyl cyanoacetate (50 mmole), 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 mmole), 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 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/petroleum ether. The purified oil solidified on standing at room tempera-ture.

後処理

  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)
  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/petroleum ether

出典と根拠

ORDレコード
ord-51037baff34b4c6a93219cef0f9aa86f
出典データセット
uspto-grants-2006_09
特許番号
US07101905B2

関連ノート

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