Water → 1-Methoxy-4-(4-nnethyltridec-2-enyl)benzene

Temperature

65 °C

p-Methoxyphenethyltriphenylphosphonium bromide (3.40 g, 7.12 mmol, 1.0 equiv.) in THF (14 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 4.5 mL, 7.12 mmol, 1.0 equiv.) at 0° C., the red solution was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 2-methylundecanal (1.97 g, 10.7 mmol, 1.5 equiv.) in THF (6 mL) was added, and the mixture was stirred at 70° C. for 14 h. After addition of H2O, the aqueous layer was extracted with cyclohexane (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 98:2) to yield 1.36 g (63%) of the title compound as a light yellow oil.

1. temperatureThe mixture was re-cooled to 0° C.
2. stirringthe mixture was stirred at 70° C. for 14 h
3. extractionthe aqueous layer was extracted with cyclohexane (2×)
4. washthe combined organic phases were washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 98:2)

ORD record

ord-a8baf3c201d84d27ac15d11af84707e7

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193935B2