Hydrochloric Acid → HCID 89526051, compound

HRID 1466155Notes

Reaction equation

HRID 1466155 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.C([O:14][CH:15](OCC)[CH:16]=[CH2:17])C.C([O-])([O-])=O.[K+].[K+].[Cl-].[K+].Cl>CN(C=O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:9]=[C:6]1[C:5]2[CH:10]=[CH:11][C:2](/[CH:17]=[CH:16]/[CH:15]=[O:14])=[CH:3][C:4]=2[CH2:8][O:7]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4873Potassium ChlorideHCID 11430Potassium CarbonateHCID 624773,3-Diethoxy-1-propeneHCID 6031445-Bromophthalide

Product 1

HCID 89526051HCID 89526051, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 5-Bromo-2-benzofuran-1(3H)-one (20 g, 94 mmol) in DMF (500 mL) was added Acrolein diethyl acetal (37 g, 282 mmol), Bu4NOAc (57 g, 188 mmol), K2CO3 (19.5 g, 141 mmol), KCl (7.0 g, 94 mmol) and Pd(OAc)2 (200 mg). The mixture was stirred for 2.5 hours at 90° C. After the mixture was cooled, 2 N HCl was slowly added and the resulting reaction mixture was stirred at room temperature for 10 min, and diluted with EtOAc, washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified with silica gel chromatography (petrol ether/EtOAc=2:1) to give title product.

Workup

  1. temperatureAfter the mixture was cooled
  2. customthe resulting reaction mixture
  3. stirringwas stirred at room temperature for 10 min
  4. washwashed with water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified with silica gel chromatography (petrol ether/EtOAc=2:1)

Sources & evidence

ORD record
ord-040b2cd78d0f43f0842ff90a42eea094
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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