Toluene → HCID 57577797, compound

HRID 1510919Notes

Reaction equation

HRID 1510919 reaction equation
C[C:2]1[C:3]([C:8]2C=CC=CC=2)=[N:4]C=[CH:6][CH:7]=1.C(O[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)C.[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:33]CN(CC)CC>CCOC(C)=O.CCCCCC>[CH3:8][C:3]1[CH:2]=[CH:7][CH:6]=[C:32]([C:26]2[C:31](/[CH:18]=[CH:19]/[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:33])[N:4]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471Triethylamine2×HCID 663023-Methyl-2-phenylpyridineHCID 1145762-Phenylvinyl acetate

Product 1

HCID 57577797HCID 57577797, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 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), 3-methyl-2-phenylpyridine (1 mmol, 183.3 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 60 hours. 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=250 mm; hexane:EtOAc:Et3N=9:1:0.1; mL each).

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 60 hours
  10. waitThe reaction solution was left
  11. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-931629eac1d946b1935bac0ae1155465
Source dataset
uspto-grants-2012_07
Patent number
US08212048B2

Reaction notes

Loading…