Tert-butyl 4-[2-(4-(2-phenylethenyl)-3-pyridyl)ethynyl]benzoate → Tert-butyl 4-[2-(4-phenethyl-3-pyridyl)ethyl]benzoate

HRID 355797Notes

Reaction equation

HRID 355797 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:15]#[C:16][C:17]2[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.C1COCC1.[Pd]>[CH2:8]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[CH:28][CH:29]=1)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 54016878Tert-butyl 4-[2-(4-(2-phenylethenyl)-3-pyridyl)ethynyl]benzoate

Product 1

HCID 22675531Tert-butyl 4-[2-(4-phenethyl-3-pyridyl)ethyl]benzoateYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

tert-Butyl 4-[2-(4-(2-phenylethenyl)-3-pyridyl)ethynyl]benzoate (0.360 g, 0.95 mmol) was dissolved in ethanol/THF 1:1 (10 ml) and treated with palladium on carbon (10%, 0.13 g). The reaction was placed under a hydrogen atmosphere and stirred at ambient temperature for 6 hours. The reaction was then filtered and evaporated to give tert-butyl 4-[2-(4-phenethyl-3-pyridyl)ethyl]benzoate (0.36 g).

Workup

  1. filtrationThe reaction was then filtered
  2. customevaporated

Sources & evidence

ORD record
ord-0ed0908341f54aeca0063ebc89f8fbbb
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

Loading…