Vanillin → HCID 22997596, compound

HRID 1713273Notes

Reaction equation

HRID 1713273 reaction equation
O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].C(N([CH2:17][CH3:18])CC)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[C:18]1[CH:17]=[CH:4][CH:3]=[CH:2][CH:9]=1)[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 1183VanillinHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 22997596HCID 22997596, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 4-hydroxy-3-methoxy-benzaldehyde (1.00 g) in dichloromethane (22 mL) was added triethylamine (1.37 mL). Then trifluoromethanesulfonic anhydride (1.40 mL) was added dropwise, and the resulting mixture was stirred under ice-cooling for 45 minutes. Ice was added and the whole was partitioned between AcOEt (60 mL) and saturated aqueous sodium hydrogen carbonate (30 mL). The organic layer was washed successively with water/brine (3/1, 40 mL) and brine (30 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue (1.98 g) was dissolved in N,N-dimethylformamide (25 mL). Phenylboronic acid (0.882 g), sodium carbonate (1.39 g), water (5 mL) and tetrakis(triphenyl-phosphine)palladium(0) (0.380 g) were added, and the resulting mixture was stirred at 80° C. for 2.5 hours. The reaction mixture was cooled to room temperature and then partitioned between ethyl acetate (70 mL) and water (30 mL). The organic layer was washed with water/brine (1/1, 30 mL×2), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1 to 5/1) to give the title compound (1.12 g).

Workup

  1. temperaturecooling for 45 minutes
  2. additionIce was added
  3. customthe whole was partitioned between AcOEt (60 mL) and saturated aqueous sodium hydrogen carbonate (30 mL)
  4. washThe organic layer was washed successively with water/brine (3/1, 40 mL) and brine (30 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue (1.98 g) was dissolved in N,N-dimethylformamide (25 mL)
  8. additionPhenylboronic acid (0.882 g), sodium carbonate (1.39 g), water (5 mL) and tetrakis(triphenyl-phosphine)palladium(0) (0.380 g) were added
  9. stirringthe resulting mixture was stirred at 80° C. for 2.5 hours
  10. custompartitioned between ethyl acetate (70 mL) and water (30 mL)
  11. washThe organic layer was washed with water/brine (1/1, 30 mL×2)
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1 to 5/1)

Sources & evidence

ORD record
ord-04eb812907444b12a2ca97a19b5c9b47
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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