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

HRID 1416423

反応式

HRID 1416423 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

In an autoclave, 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, and 0.30 g (1.6 mmol) of cobaltocene (=dicyclopentadienylcobalt; Aldrich, Milwaukee/USA) is added. Then an acetylene pressure of 15 atm is applied, and the mixture is heated to 180° C. and stirred for 12 h. 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 by column chromatography (SiO2, hexane/ethyl acetate 19:1→4:1) of the mother liquor.

後処理

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

出典と根拠

ORDレコード
ord-a328bdec712342d89e2fe215d2b32c52
出典データセット
uspto-grants-1999_06
特許番号
US05912352

関連ノート

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