Pyridine-2-acetonitrile → 2-(2-Pyridyl)-3-(3,5-di-tert-butylphenyl)-2-propenenitrile

HRID 1489154Notes

Reaction equation

HRID 1489154 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]#[N:25]>C(O)C.N1CCCCC1>[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[CH:8][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=1)[C:24]#[N:25]

Participants

5

Reactant 2

HCID 75959Pyridine-2-acetonitrileHCID 12682533,5-Bis(tert-butyl)benzaldehyde

Product 1

HCID 537161712-(2-Pyridyl)-3-(3,5-di-tert-butylphenyl)-2-propenenitrile

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 2.0 g (9.17 mmole) 3,5-di-tert -butylbenzaldehyde in 75 ml absolute ethanol are added 1.19 g (10.1 mmole) 2-pyridylacetonitrile and 12 drops piperidine. The reaction flask is equipped with a condenser and a drying tube (using anhydrous CaSO4), and the reaction is stirred and heated. After refluxing for 8 hours, the reaction is allowed to cool to room temperature and stirred overnight for 16 hours. The solvent is removed by rotary evaporation, and the residue purified by flash chromatography on silica gel, eluting with hexane-ethyl acetate, 98:2. The colorless solid is washed with cold ether-hexane to give 2-(2-pyridyl)-3-(3,5-di-tert-butylphenyl)-2-propenenitrile, m.p. 90°-93° C.

Workup

  1. temperatureheated
  2. temperatureAfter refluxing for 8 hours
  3. stirringstirred overnight for 16 hours
  4. customThe solvent is removed by rotary evaporation
  5. customthe residue purified by flash chromatography on silica gel
  6. washeluting with hexane-ethyl acetate, 98:2
  7. washThe colorless solid is washed with cold ether-hexane

Sources & evidence

ORD record
ord-c3981c08a8084fe39daa768ec389a8e7
Source dataset
uspto-grants-1997_10
Patent number
US05677329

Reaction notes

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