Reaktion #2324253

Reaktionsgleichung

bromodecane

potassium tert-butoxide

ethynylnaphthalene

n-butyl lithium

→

1-ethynyl-2-n-decylnaphthalene

Ausbeute 35.9%

Lösungsmittel

diethyl ether

tetrahydrofuran

water

hexane

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe temperature was raised up to 5° C
2. 2
   workup.STIRRINGstirred at 20° C. for 2 hours
3. 3
   Extraktionto extract the generated compound
4. 4
   WaschenThe diethyl ether layer was washed with 50 mL of distilled water for 3 times
5. 5
   Trocknendried over anhydrous magnesium sulfate for 1 hour
6. 6
   Filtrationfollowed by filtration
7. 7
   Sonstigethe solvent was removed by evaporation
8. 8
   SonstigeThe resulting product was purified on a column

Vorschrift

To 25 mL of a tetrahydrofuran solution of 3.05 g of ethynylnaphthalene was added 27.5 mL of a 1.6 mol/L hexane solution of n-butyl lithium at −50° C. under a nitrogen atmosphere, and the mixture was cooled to −80° C., and then 15 mL of a tetrahydrofuran solution of 2.25 g of potassium tert-butoxide was added thereto. After stirring at −80° C. for 1 hour, the temperature was raised up to 5° C. At −70° C., 4.42 g of bromodecane was dropped to the resulting solution, and stirred at 20° C. for 2 hours. After addition of 150 mL of diethyl ether at 0° C., 50 mL of water was dropped to the resulting solution to extract the generated compound. The diethyl ether layer was washed with 50 mL of distilled water for 3 times, dried over anhydrous magnesium sulfate for 1 hour, followed by filtration, and the solvent was removed by evaporation. The resulting product was purified on a column using hexane as a developing solvent, thereby 2.1 g of 1-ethynyl-2-n-decylnaphthalene was obtained. The obtained 1-ethynyl-2-n-decylnaphthalene was analyzed by 1H-NMR (270 MHz, CDCl3), and the NMR spectra showed peak at δ 8.3 (1H), 7.8 (2H), 7.5 (3H), 3.6 (1H), 3.0 (2H) 1.7 (2H), 1.3 (16H), 0.9 (3H).

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