Reaktion #1532180

Reaktionsgleichung

2-formyl-3-methyl-4-cyclohexylthiophene

n-BuLi

hexane

→

2-vinyl-3-methyl-4-cyclohexylthiophene

Ausbeute 50.0%

Lösungsmittel

ether

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas warmed to room temperature
2. 2
   workup.STIRRINGThe solution was stirred overnight
3. 3
   Waschenwashed with water and brine
4. 4
   Trocknendried over MgSO4
5. 5
   SonstigeThe solvent was removed in vacuo
6. 6
   Sonstigethe crude product was purified by column chromatography

Vorschrift

To a solution of methyltriphenylphosphonium bromide (4.983 g, 13.96 mmol) in ether at 0° C. was added dropwise 1.6 M n-BuLi solution in hexane (8.7 ml, 13.96 mmol). The solution was stirred at 0° C. for 40 min and then was warmed to room temperature. A solution of 2-formyl-3-methyl-4-cyclohexylthiophene dimer (2.7 g, 6.98 mmol) in a minimum of ether was added. The solution was stirred overnight. The reaction mixture was then diluted with ether and washed with water and brine, and dried over MgSO4. The solvent was removed in vacuo and the crude product was purified by column chromatography using hexane as the eluant to afford 2-vinyl-3-methyl-4-cyclohexylthiophene dimer 1.32 g (50% yield) as a white solid. 1H NMR (CDCl3) δ 6.98 (s, 1H), 6.90 (dd, 1H), 5.52 (d, 1H), 1.15 (d, 1H), 2.22 (s, 1H), 2.19 (s, 1H), 2.11 (s, 1H), 2.10 (s, 1H), 2.09 (s, 1H), 2.08 (s, 1H). 13C NMR (CDCl3) δ 147.93, 146.37, 137.41, 136.09, 134.78, 129.97, 128.44, 127.57, 118.61, 112.7, 40.07, 38.86, 33.74, 31.37, 27.19, 26.91, 26.30, 26.12, 13.61, 13.33.

Quelle