反応 #805720

反応方程式

H2O

n-BuLi

benzyltriphenylphosphonium bromide

2-methylundecanal

→

title compound

収率 76.0%

(3-Methyldodec-1-enyl)benzene

収率 76.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   温度The mixture was re-cooled to 0° C.
2. 2
   workup.STIRRINGthe mixture was stirred at 65° C. for 18 h
3. 3
   抽出the aqueous layer was extracted with cyclohexane (2×)
4. 4
   洗浄the combined organic phases were washed with brine
5. 5
   乾燥dried (MgSO4)
6. 6
   ろ過filtered
7. 7
   濃縮the filtrate was concentrated
8. 8
   その他The residue was purified by flash chromatography on SiO2 (cyclohexane)

実験手順

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.

出典