Allyl Alcohol → 3-(4-Acetamidophenyl)propanal

HRID 1242263Notes

Reaction equation

HRID 1242263 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[CH2:17]([OH:20])[CH:18]=[CH2:19]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[Pd]Cl.CN(C=O)C>[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:19][CH2:18][CH:17]=[O:20])=[CH:3][CH:4]=1)(=[O:11])[CH3:10]

Participants

7

Reactant 3

HCID 7858Allyl AlcoholHCID 12147N-(4-Iodophenyl)acetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 99206073-(4-Acetamidophenyl)propanalYield 23.9%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 70681Tetrabutylammonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-(4-Iodophenyl)acetamide (10.8 g, 42 mmol, 1.0 equiv) and DMF (50.0 ml) were added tetrabutylammonium chloride (11.7 g, 42 mmol, 1.0 equiv), NaHCO3 (8.7 g, 105 mmol), and allyl alcohol (4.2 ml, 63 mmol, 1.5 equiv) and the mixture was stirred for 10 min. To the resulting mixture PdCl2 (1.21 g, 9.6 mmol, 0.23 equiv) was added and the mixture was stirred under nitrogen for 45 h. The resulting mixture was extracted with EtOAc (3×100 ml). The combined extracts were washed with 5% HCl, brine, dried over MgSO4 and concentrated under vacuum. The residue was purified by column chromatography (EtOAc:hexane 70:30) to give 3-(4′-Acetamidophenyl)-1-propanal (1.92 g, 23.1%) which was used as such in the next step.

Workup

  1. stirringthe mixture was stirred under nitrogen for 45 h
  2. extractionThe resulting mixture was extracted with EtOAc (3×100 ml)
  3. washThe combined extracts were washed with 5% HCl, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (EtOAc:hexane 70:30)

Sources & evidence

ORD record
ord-e41e43ed183141d2bfe6d5f6ae3ede99
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

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