Toluene → Methyl 4-(pyridin-2-YL)benzoate

HRID 1458482

反応式

HRID 1458482 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1.C#C.[C:15]1(C)[CH:20]=CC=[CH:17][CH:16]=1>[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Co+2]>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:20][N:11]=2)=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 1140Toluene2 回HCID 6326AcetyleneHCID 70791Methyl 4-cyanobenzoate

生成物 1

HCID 3358924Methyl 4-(pyridin-2-YL)benzoate

試薬・触媒・溶媒 1

HCID 92884Cobaltocene触媒

反応条件

温度
180 °C

実験手順

24.0 g (150 mmol) of 4-cyanobenzoic acid methyl ester (Fluka, Buchs, Switzerland) in 150 ml of toluene are placed under an acetylene atmosphere in an autoclave and 0.30 g (1.6 mmol) of cobaltocene (=dicyclopentadienylcobalt; Aldrich, Milwaukee, USA) is added. The mixture is then subjected to an acetylene pressure of 15 atm, heated at 180° C. and stirred for 12 hours. After cooling and release of the pressure, 9.5 g of active carbon are added to the black suspension; the mixture is diluted with 250 ml of toluene, stirred for 30 min, filtered and concentrated by evaporation. Crystallisation from warm ether by the addition of hexane yields the title compound: m.p. 96° C.; TLC (hexane/ethyl acetate 4:1): Rf =0.37; FAB MS (M+H)+ =214. Further product can be obtained from the mother liquor by column chromatography (SiO2, hexane/ethyl acetate 19:1→4:1).

後処理

  1. additionis added
  2. temperatureAfter cooling
  3. additionrelease of the pressure, 9.5 g of active carbon are added to the black suspension
  4. stirringstirred for 30 min
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customCrystallisation
  8. temperaturefrom warm ether
  9. additionby the addition of hexane

出典と根拠

ORDレコード
ord-ae803657347f4cf7b6f38d5c6ce935af
出典データセット
uspto-grants-1998_12
特許番号
US05849911

関連ノート

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