Ethyl Acetate → HCID 67326976, compound

HRID 881784Notes

Reaction equation

HRID 881784 reaction equation
[CH:1]([CH:3]([C:10]#[N:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2].[C:12]1([N:18]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:19]2[CH:26]=[CH:25]C(C=O)=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1CC[CH2:35][CH2:34]1.CC(=O)OCC>CO>[C:27]1([N:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:19]2[CH:26]=[CH:25][C:2](/[CH:1]=[C:3](/[C:4]3[CH:9]=[CH:8][C:7]([CH:34]=[CH2:35])=[CH:6][CH:5]=3)\[C:10]#[N:11])=[CH:21][CH:20]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 147675092-Phenylbut-3-enenitrile2×

Product 1

HCID 67326976HCID 67326976, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Vinyl benzylcyanide (2.2 g, 0.0154 mol) was dissolved in methanol (10 mL) and 4-(diphenylamino)benzaldehyde (1 ME, 0.0154 mol, 4.2 g) was added, followed by the addition of pyrrolidine (1.5 ME, 0.0231 mol, 1.64 g, 1.9 mL). The resulting reaction mixture was heated at reflux overnight under argon. TLC analysis on the mixture (H:EA, 8.5:1.5) showed the formation of a yellow coloured product along with some unreacted vinyl benzylcyanide. The reaction mixture was purified by column chromatography (hexane:ethyl acetate, 8.5:1.5). After chromatography, the pure product, AG1-78, was obtained as a yellow colloured brightly fluorescent material solid (1.5 g, 23%), 1H NMR (400 MHz, CDCl3) δ 5.3 (d, 1H, ethylene —CH), δ5.8 (d, 1H, ethylene-CH), δ 6.7 (m, 1H), δ 7.1 (m, 8H), δ 7.3 (m, 4H), δ 7.45 (m, 3H), δ 7.6 (dd, 2H), δ 7.7 (dd, 2H), 13C NMR (CDCl3, ppm, δ): 149.94, 146.60, 141.18, 137.85, 135.97, 134.34, 130.66, 129.56, 126.75, 126.44, 125.78, 125.70, 124.37, 120.89, 118.66, 114.81, 107.38.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux overnight under argon
  4. customThe reaction mixture was purified by column chromatography (hexane:ethyl acetate, 8.5:1.5)

Sources & evidence

ORD record
ord-34539d98f7d04fe3875c1de363b11c67
Source dataset
uspto-grants-2015_03
Patent number
US08993697B2

Reaction notes

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