Ethyl propiolate → HCID 86652418、化合物

HRID 1040402ノート

反応式

HRID 1040402 の反応式
[N:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])=[N+:2]=[N-:3].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[C:13]#[CH:14]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N:1]1[CH:14]=[C:13]([C:12]([O:16][CH2:17][CH3:18])=[O:15])[N:3]=[N:2]1)=[O:7].[CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N:1]1[C:13]([C:12]([O:16][CH2:17][CH3:18])=[O:15])=[CH:14][N:3]=[N:2]1)=[O:7]

参加物

7

反応物 2

HCID 12182Ethyl propiolate2 回HCID 108880602-Azidobenzaldehyde

生成物 2

HCID 86652418HCID 86652418、化合物収率 66%HCID 86652419HCID 86652419、化合物収率 17%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-azidobenzaldehyde (100 mg, 0.68 mmol) in 1.0 mL of dry N,N-dimethylformamide was added ethyl propiolate (0.14 mL, 1.4 mmol) at room temperature. After being stirred at 100° C. for 12 h, ethyl propiolate (0.14 mL, 1.4 mmol) was added again with additional stirring for 12 h. After cooling, the reaction mixture was diluted with a 5:1 solution (12 mL) of ethyl acetate and hexane. The solution was washed with water twice, brine, and dried over Na2SO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25) to obtain ethyl 1-(2-formylphenyl)-1H-1,2,3-triazol-4-carboxylate as a crystal (111 mg, 66%) and ethyl 1-(2-formylphenyl)-1H-1,2,3-triazol-5-carboxylate as a oil (28 mg, 17%).

後処理

  1. stirringwith additional stirring for 12 h
  2. temperatureAfter cooling
  3. washThe solution was washed with water twice
  4. dry with materialbrine, and dried over Na2SO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25)

出典と根拠

ORDレコード
ord-b8c4a077bec34deb85e99db9cd3bb316
出典データセット
uspto-grants-2013_10
特許番号
US08552220B2

反応ノート

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