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

HRID 2105572Notes

Reaction equation

HRID 2105572 reaction equation
C([C:3]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][C:7](OC)=O)=O.O[C:19]1[CH:26]=[CH:25][C:24]([N+]([O-])=O)=[CH:23][C:20]=1[CH:21]=O.[OH-].[K+].[CH3:32][CH2:33][OH:34]>>[O:5]1[CH:6]=[CH:7][C:11]2[CH:12]=[C:13]([NH:15][C:33](=[O:34])/[CH:32]=[CH:21]/[C:20]3[CH:23]=[CH:24][C:25]([C:20]([CH3:23])([CH3:21])[CH3:19])=[CH:26][CH:19]=3)[CH:14]=[CH:3][C:4]1=2

Participants

5

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 668085-NitrosalicylaldehydeHCID 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
65 °C

Procedure

Methyl 2-(2-formyl-4-nitrophenoxy)acetate. To a round-bottomed flask was added a suspension of 2-hydroxy-5-nitrobenzaldehyde (10 g, 60 mmol, Aldrich) in anhydrous EtOH (180 mL). The suspension was treated with KOH (4.4 g, 66 mmol) and heated under N2 with magnetic stirring in a 65° C. oil bath for 45 min. The reaction mixture was allowed to cool to 25° C. and concentrated in vacuo. Anhydrous DMF (180 mL) was added, and the reaction flask was cooled in an ice bath and charged with methyl bromoacetate (10 mL, 110 mL, Aldrich). The reaction mixture was stirred for 3.5 h at 25° C., then the solvent was removed in vacuo. Water (200 mL) was added, and the mixture was extracted with EtOAc (3×50 mL). The combined organic extract was washed with 1 M H3PO4, satd NaHCO3, and satd NaCl. After drying over MgSO4, the organic layer was filtered and concentrated in vacuo. The residue was recrystallized from CH2Cl2 and hexane to afford the title product as a pale yellow solid. MS (ESI, pos. ion) m/z: 240 (M+1).

Workup

  1. additionTo a round-bottomed flask was added
  2. temperatureheated under N2
  3. temperatureto cool to 25° C.
  4. concentrationconcentrated in vacuo
  5. additionAnhydrous DMF (180 mL) was added
  6. temperaturethe reaction flask was cooled in an ice bath
  7. additioncharged with methyl bromoacetate (10 mL, 110 mL, Aldrich)
  8. stirringThe reaction mixture was stirred for 3.5 h at 25° C.
  9. customthe solvent was removed in vacuo
  10. additionWater (200 mL) was added
  11. extractionthe mixture was extracted with EtOAc (3×50 mL)
  12. extractionThe combined organic extract
  13. washwas washed with 1 M H3PO4
  14. dry with materialAfter drying over MgSO4
  15. filtrationthe organic layer was filtered
  16. concentrationconcentrated in vacuo
  17. customThe residue was recrystallized from CH2Cl2 and hexane

Sources & evidence

ORD record
ord-23b175ae87fc4201a694b3d24f2b8e14
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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