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

HRID 2105573Notes

Reaction equation

HRID 2105573 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Conditions

Temperature
25 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-de3bc357770c4ecf89f1c8a276831020
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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