Acetic Acid → 1-Isopropyl-3-[5-(4-methoxyphenyl)pent-4-en-2-yl]benzene

Potassium t-butylat (17.1 mL, 17.1 mmol, 1.0 equiv., 1M in THF) was added to a solution of (4-methoxyphenyl)methyltriphenylphosphonium bromide (7.90 g, 17.1 mmol, 1.0 equiv.) in THF (17 mL) at 25° C. After the dark red suspension was stirred at 25° C. for 10 min, 3-(3-isopropylphenyl)butanal (3.24 g, 17.1 mmol, 1.0 equiv.) in THF (8.5 mL) was added, and the mixture was stirred at 25° C. 12 h. After addition of 20% aq. AcOH-solution at 25° C., the aqueous layer was extracted with hexane. The combined organic phases were washed with MeOH/H2O (4:1; 2-3x), dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 995:5→99:1) to yield 4.03 g (80%) of the title compound as a light yellow oil.

1. stirringthe mixture was stirred at 25° C
2. custom12 h
3. extractionthe aqueous layer was extracted with hexane
4. washThe combined organic phases were washed with MeOH/H2O (4:1; 2-3x)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 995:5→99:1)

ORD-Eintrag

ord-236b0b9155ef4a1eaf7301b3112c7839

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09193935B2