Toluene → HCID 67528933, compound

HRID 1510916Notes

Reaction equation

HRID 1510916 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.C1(C)C=CC=CC=1>CCN(CC)CC.CCOC(C)=O.CCCCCC>[CH:17]([C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 138872-PhenylpyridineHCID 1145762-Phenylvinyl acetate

Product 1

HCID 67528933HCID 67528933, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 8471TriethylamineSolvent2×HCID 8857Ethyl AcetateSolvent

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 (3 mmol, 486.6 mg) and toluene (1.5 mL) were added. The mixture was heated by an oil bath and reacted under reflux condition for 32 hours. 32 hours after, the reaction solution was left to cool to room temperature, then, triethylamine (0.3 mL) was added. Isolation of the product was carried out by silica gel column chromatography (i.d.=30 mm; length=170-250 mm; hexane:EtOAc:Et3N=9:1:0.1; 25 mL each). A subject substance 2-(2-styrylphenyl)-pyridine was obtained with a yield of 69%.

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 32 hours
  10. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-612f30add2ae4af1b788e75527e808e2
Source dataset
uspto-grants-2012_07
Patent number
US08212048B2

Reaction notes

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