Acetic Acid → Ethyl 2-cyano-3-phenyl-2-butenoate

HRID 1248469ノート

反応式

HRID 1248469 の反応式
F[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(O)(=O)C>C1C=CC=CC=1.O>[C:11]([C:13](=[C:8]([CH3:9])[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 98284'-FluoroacetophenoneHCID 517165Ammonium Acetate

生成物 1

HCID 29024Ethyl 2-cyano-3-phenyl-2-butenoate収率 69.9%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒2 回HCID 962Water溶媒

実験手順

A mixture of p-fluoroacetophenone (100 g, 0.72 mole), ethyl cyanoacetate (81.8 g, 0.72 mole), ammonium acetate (13 g, 0.17 mole) and acetic acid (34.7 g, 0.57 mole) is refluxed for 24 hours in benzene (200 mL) with a continuous removal of water by a Dean Stark trap. The cooled mixture is diluted with benzene (150 mL) and extracted with water (2×300 mL). The organic phase is separated, dried (Na2SO4), filtered and concentrated in vacuo to a brown oil. Kugelrohr distillation (125°-127°/0.03 Torr.) affords 108.4 g (64.3%) of product as a yellow green oil.

後処理

  1. extractionextracted with water (2×300 mL)
  2. customThe organic phase is separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a brown oil
  6. distillationKugelrohr distillation (125°-127°/0.03 Torr.)

出典と根拠

ORDレコード
ord-fef0c1c04bb04a6c8b1f27cbeb97caab
出典データセット
uspto-grants-1985_06
特許番号
US04524206

反応ノート

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