Toluene → HCID 68938830, compound

HRID 1510915Notes

Reaction equation

HRID 1510915 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=O)C.[C:25]1([CH3:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:32](N(CC)CC)C>>[CH:32]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH:17]=[CH:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:1]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[CH:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 138872-PhenylpyridineHCID 1145762-Phenylvinyl acetate

Product 1

HCID 68938830HCID 68938830, compoundYield 93%

Procedure

A Teflon-coated magnetic stirring rod was placed in a 10 mL two-necked flask which was then equipped with a reflux condenser. The reflux condenser was connected to a pressure reduced/nitrogen line and the whole apparatus was dried with heating under reduced pressure. Thereafter, N2 gas was charged in the reaction apparatus and the whole reaction apparatus was purged with nitrogen. The reaction vessel was left to cool to room temperature, then, Ru(cod)(cot) complex (0.05 mmol, 15.8 mg), 2-phenylpyridine (1 mmol, 155.2 mg), styryl acetate (5 mmol, 811.0 mg) and toluene (1.5 mL) were added. The mixture was heated by an oil bath and reacted under reflux condition for 72 hours. 72 hours after, the reaction solution was left to cool to room temperature, then, triethylamine (0.3 mL) was added to make it basic, and the reaction mixture was purified by silica gel column chromatography (i.d.=30 mm; length=170-250 mm; hexane:EtOAc:Et3N=8:1:0.1; 25 mL each). A subject substance 2-(2,6-distyrylphenyl)-pyridine was obtained with a yield of 93%.

Workup

  1. customwhich was then equipped with a reflux condenser
  2. customthe whole apparatus was dried
  3. temperaturewith heating under reduced pressure
  4. additionThereafter, N2 gas was charged in the reaction apparatus
  5. customthe whole reaction apparatus was purged with nitrogen
  6. waitThe reaction vessel was left
  7. temperatureThe mixture was heated by an oil bath
  8. customreacted
  9. temperatureunder reflux condition for 72 hours
  10. temperatureto cool to room temperature
  11. customthe reaction mixture was purified by silica gel column chromatography (i.d.=30 mm; length=170-250 mm; hexane:EtOAc:Et3N=8:1:0.1; 25 mL each)

Sources & evidence

ORD record
ord-679dcc088f72441eb08be8dd7c9d60f3
Source dataset
uspto-grants-2012_07
Patent number
US08212048B2

Reaction notes

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