Allyl Alcohol → 3-(4-Acetamidophenyl)propanal

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.

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)

ORD record

ord-e41e43ed183141d2bfe6d5f6ae3ede99

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115666B2