Ethanol → (2E)-N-Benzo[b]furan-5-yl-3-[4-(tert-butyl)phenyl]prop-2-enamide

HRID 730268

反応式

HRID 730268 の反応式
[N+]([C:4]1[CH:5]=[CH:6][C:7]2O[C:10]([C:12]([O:14]CC)=O)=[CH:9][C:8]=2[CH:17]=1)([O-])=O.C([C:20]1[CH:31]=[C:30]([N+:32]([O-])=O)[CH:29]=[CH:28][C:21]=1[O:22][CH2:23][C:24](OC)=O)=O.[CH3:35]CO.N12[CH2:48][CH2:47][CH2:46]N=C1CCCCC2>>[O:22]1[CH:23]=[CH:24][C:28]2[CH:29]=[C:30]([NH:32][C:12](=[O:14])/[CH:10]=[CH:9]/[C:8]3[CH:17]=[CH:4][C:5]([C:47]([CH3:48])([CH3:35])[CH3:46])=[CH:6][CH:7]=3)[CH:31]=[CH:20][C:21]1=2

参加物

5

反応物 4

HCID 702EthanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13829542-Benzofurancarboxylic acid, 5-nitro-, ethyl esterHCID 43415506Acetic acid, 2-(2-formyl-4-nitrophenoxy)-, methyl ester

生成物 1

HCID 10193291(2E)-N-Benzo[b]furan-5-yl-3-[4-(tert-butyl)phenyl]prop-2-enamide

反応条件

温度
25 °C

実験手順

Ethyl 5-nitrobenzo[d]furan-2-carboxylate. To a 250 mL round-bottomed flask was added methyl 2-(2-formyl-4-nitrophenoxy)acetate, Example 38(a), (5.3 g, 22 mmol), EtOH (110 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (3.7 g, 24 mmol, Aldrich). The reaction mixture was magnetically stirred at 25° C. for 20 h, then concentrated to approximately half of its volume in vacuo. After cooling the mixture in an ice bath for 20 min, a precipitate formed which was collected by filtration and washed with ice cold EtOH. The resulting pale yellow solid was dried in vacuo to provide the title product. MS (ESI, pos. ion) m/z: 253 (M+H2O).

後処理

  1. concentrationconcentrated to approximately half of its volume in vacuo
  2. temperatureAfter cooling the mixture in an ice bath for 20 min
  3. customa precipitate formed which
  4. filtrationwas collected by filtration
  5. washwashed with ice cold EtOH
  6. customThe resulting pale yellow solid was dried in vacuo

出典と根拠

ORDレコード
ord-0737113ed5914b41afbd87fc3477dff8
出典データセット
uspto-grants-2009_09
特許番号
US07582657B2

関連ノート

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