Reaktion #805720

Reaktionsgleichung

H2O

n-BuLi

benzyltriphenylphosphonium bromide

2-methylundecanal

→

title compound

Ausbeute 76.0%

(3-Methyldodec-1-enyl)benzene

Ausbeute 76.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was re-cooled to 0° C.
2. 2
   workup.STIRRINGthe mixture was stirred at 65° C. for 18 h
3. 3
   Extraktionthe aqueous layer was extracted with cyclohexane (2×)
4. 4
   Waschenthe combined organic phases were washed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenthe filtrate was concentrated
8. 8
   SonstigeThe residue was purified by flash chromatography on SiO2 (cyclohexane)

Vorschrift

A suspension of benzyltriphenylphosphonium bromide (3.20 g, 7.38 mmol, 1.0 equiv.) in THF (14 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 4.6 mL, 7.38 mmol, 1.0 equiv.) at 0° C., the red suspension was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 2-methylundecanal (2.04 g, 11.1 mmol, 1.5 equiv.) in THF (5 mL) was added, and the mixture was stirred at 65° C. for 18 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) to yield 1.45 g (76%) of the title compound as a colorless oil.

Quelle