Ethyl Acetate → HCID 69203345, compound

HRID 2378221Notes

Reaction equation

HRID 2378221 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[NH2:10][C:11]1[CH:12]=[C:13]([C:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH2:32][CH3:33])[CH:24]=2)=[CH:20][C:21]#[N:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH2:32]([O:31][C:25]1[CH:24]=[C:23]([C:19]([C:13]2[CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:11]([N:10]3[CH:3]=[CH:7][CH:6]=[CH:5]3)[CH:12]=2)=[CH:20][C:21]#[N:22])[CH:28]=[CH:27][C:26]=1[O:29][CH3:30])[CH3:33]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 69204282HCID 69204282, compound

Product 1

HCID 69203345HCID 69203345, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,5-Dimethoxytetrahydrofuran (0.2 g, 1.7 mmol) was added to a stirred solution of 3-(3-amino-4-methoxy-phenyl)-3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile (0.5 g, 1.5 mmol) in acetic acid (10 mL). The reaction mixture was heated to reflux under nitrogen for one hour. The mixture was cooled down to room temperature. The mixture was stirred with EtOAc (100 mL) and saturated NaHCO3 (40 mL) was added slowly. The EtOAc solution was washed with water (60 mL), brine (60 mL) and dried (MgSO4). Solvent was removed and the residue was purified by flash chromatography (silica gel, Hexane:EtOAc 6:4) to afford mixture of isomers of 3-(3-ethoxy-4-methoxy-phenyl)-3-(4-methoxy-3-pyrrol-1-yl-phenyl)-acronitrile (0.4 g, 60%) as a white solid: mp 109-111° C.; 1H NMR (CDCl3) δ 7.00 (m, 2H), 7.47-6.81 (m, 6H), 6.30 (m, 2H), 5.59 (5.57) (s, 1H), 4.05 (m, 2H), 3.91 (m, 6H), 1.45 (m, 3H); 13C NMR (CDCl3) δ 161.67(161.61), 153.93(154.35), 151.56(151.00), 148.27(148.00), 131.40(132.10), 129.83(130.06), 129.03(127.16), 125.93(127.93), 123.07, 122.21, 122.05(121.93), 118.52(118.43), 114.00, 112.01(112.06), 111.09(112.70), 109.15(109.28), 92.45, 64.56, 56.05(56.00), 14.69; Anal. Calcd for C23H22N2O3. Theoretical: C, 73.78; H, 5.92, N, 7.48. Found: C, 73.46; H, 5.71; N, 7.35.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under nitrogen for one hour
  3. additionwas added slowly
  4. washThe EtOAc solution was washed with water (60 mL), brine (60 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed
  7. customthe residue was purified by flash chromatography (silica gel, Hexane:EtOAc 6:4)
  8. customto afford
  9. additionmixture of isomers of 3-(3-ethoxy-4-methoxy-phenyl)-3-(4-methoxy-3-pyrrol-1-yl-phenyl)-acronitrile (0.4 g, 60%) as a white solid

Sources & evidence

ORD record
ord-384f76ffc9954077a38fe8e312640f97
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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