Hydrochloric Acid → HCID 13170167, compound

HRID 501814Notes

Reaction equation

HRID 501814 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([O-])(=O)C.[K+].[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16].Cl>CN(C)C=O.C(OCC)(=O)C=C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2](/[CH:10]=[CH:16]/[C:15]([O:18][CH2:19][CH3:20])=[O:17])=[CH:3][CH:4]=1)=[O:7]

Participants

11

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 707414-BromobenzaldehydeHCID 517044Potassium Acetate

Product 1

HCID 13170167HCID 13170167, compound

Reagents, catalysts & solvents 6

HCID 11776TriphenylphosphineCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8821Ethyl AcrylateSolvent

Conditions

Temperature
90 °C

Procedure

5.00 g of 4-bromobenzaldehyde was dissolved in 100 mL of N,N-dimethylformamide, to which 2.9 mL of ethyl acrylate, 0.30 g of palladium(II) acetate, 0.35 g of triphenylphosphine, 13.20 g of potassium acetate, and 8.70 g of tetra-n-butylammonium bromide were added, and this solution was stirred for 2.5 hours at 90° C. The reaction mixture was added to a mixture of ethyl acetate and water, and adjusted to pH 2 with 6M hydrochloric acid, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1] to yield 4.75 g of ethyl (E)-3-(4-formylphenyl)-2-propenoate as yellow solid.

Workup

  1. additionwere added
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1]

Sources & evidence

ORD record
ord-4e85852a1c8b49a0ae98822f4bc10298
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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