Formic Acid → Ethyl 2-(3-formylphenyl)acetate

HRID 890795ノート

反応式

HRID 890795 の反応式
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#N)[CH:7]=1)[CH3:2].C(O)=[O:16]>[Al].[Ni]>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=[O:16])[CH:7]=1)[CH3:2]

参加物

4

反応物 2

HCID 284Formic AcidHCID 11194802Ethyl 2-(3-cyanophenyl)acetate

生成物 1

HCID 23076590Ethyl 2-(3-formylphenyl)acetate

試薬・触媒・溶媒 1

HCID 6336846Nickel aluminide触媒

反応条件

温度
100 °C

実験手順

To a solution of (3-cyano-phenyl)-acetic acid ethyl ester (4.8 g, 25.4 mmol) in 75% aqueous formic acid was added nickel-aluminum alloy (4.6 g). The mixture was heated at reflux (100° C.) for 2.25 h. The reaction mixture was cooled and was filtered through Celite with the aid of boiling EtOH. The filtrate was diluted with H2O and the product was extracted into CHCl3 (3×). The organic solution was stirred with saturated NaHCO3 solution until a pH of 8 was attained. The organic solution was dried over MgSO4, filtered, and concentrated. The product was purified by flash chromatography (5:1 hexanes/EtOAc) to afford the title compound (3.33 g). 1H NMR (400 MHz, CDCl3) δ 7.76–7.79 (m, 2H), 7.47–7.57 (m, 2H), 4.15 (q, 2H), 3.69 (s, 2H), 1.25 (t, 3H); MS 193 (M+1).

後処理

  1. temperatureThe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. filtrationwas filtered through Celite with the aid of boiling EtOH
  4. additionThe filtrate was diluted with H2O
  5. extractionthe product was extracted into CHCl3 (3×)
  6. dry with materialThe organic solution was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography (5:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-993fde1c79824fd78e1228e50ffbb941
出典データセット
uspto-grants-2006_02
特許番号
US06998423B2

反応ノート

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