Triethylamine → HCID 54318540, compound

HRID 369891Notes

Reaction equation

HRID 369891 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[C:21]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:24])[CH:22]=[CH2:23].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])[CH:23]=[CH:22][C:21]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 23282575Methyl 2-methoxy-4-trifluoromethane-sulfonyloxybenzoate

Product 1

HCID 54318540HCID 54318540, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of methyl 2-methoxy-4-trifluoromethanesulfonyloxybenzoate (26.8 g), t-butyl acrylate (62.5 ml), triethylamine (25 ml) in anhydrous dimethylformamide (100 ml) are added palladium acetate (0.4 g) and 1,3-bis(diphenylphosphino)propane (0.74 g) under argon atmosphere, and the mixture is heated with stirring at 75° C. for 16 hours. The reaction solution is concentrated under reduced pressure to remove the solvent, and thereto is added water. The mixture is extracted with ethyl acetate, and the extract is washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:5) to give t-butyl 3-methoxy-4-methoxycarbonylcinnamate (23.5 g).

Workup

  1. temperaturethe mixture is heated
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. customto remove the solvent
  4. additionis added water
  5. extractionThe mixture is extracted with ethyl acetate
  6. washthe extract is washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:5)

Sources & evidence

ORD record
ord-5d983ff950fe4cf687feb01d5cd0734f
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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