Hydrochloric Acid → HCID 86659249, compound

HRID 1893153Notes

Reaction equation

HRID 1893153 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C([O:19][CH:20](OCC)[CH:21]=[CH2:22])C.C(=O)([O-])[O-].[K+].[K+].[Cl-].[K+].Cl>CN(C=O)C.C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]1([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2](/[CH:22]=[CH:21]/[CH:20]=[O:19])=[CH:3][CH:4]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4873Potassium ChlorideHCID 11430Potassium CarbonateHCID 624773,3-Diethoxy-1-propeneHCID 44129579HCID 44129579, compound

Product 1

HCID 86659249HCID 86659249, compoundYield 62.8%

Reagents, catalysts & solvents 3

HCID 82707Tetrabutylammonium AcetateCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-bromo-4-(3-phenylpropyl)-benzene (684 mg, 2.48 mmol) in DMF (10 mL) were added acrolein diethyl acetal (1.7 mL, 11.1 mmol), tetrabutylammonium acetate (1.87 g, 6.2 mmol), potassium carbonate (514 mg, 3.72 mmol), potassium chloride (185 mg, 2.48 mmol), and palladium(II) acetate (50 mg, 0.22 mmol). After stirring at 90° C. for 4 h, the reaction mixture was cooled to RT and HCl (2M, 15 mL) was added. After stirring for 10 min at RT, the mixture was extracted with MTBE and washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Purification by MPLC (20% ethyl acetate in hexanes) gave 390 mg (2E)-3-[4-(3-phenylpropyl)phenyl]acrylaldehyde as a yellow oil.

Workup

  1. temperaturethe reaction mixture was cooled to RT
  2. stirringAfter stirring for 10 min at RT
  3. extractionthe mixture was extracted with MTBE
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by MPLC (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b352cee2a5804257ba17f5c30b3f69e5
Source dataset
uspto-grants-2013_08
Patent number
US08513220B2

Reaction notes

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