Reaktion #2324254

Reaktionsgleichung

bromooctadecane

potassium tert-butoxide

ethynylnaphthalene

n-butyl lithium

→

1-ethynyl-2-n-octadecylnaphthalene

Ausbeute 19.6%

Lösungsmittel

water

tetrahydrofuran

hexane

hexane

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe temperature was raised up to 5° C
2. 2
   workup.STIRRINGstirred overnight at 30° C
3. 3
   Extraktionto extract the generated compound
4. 4
   WaschenThe hexane layer was washed with 30 mL of distilled water for 3 times
5. 5
   Trocknendried over anhydrous magnesium sulfate for 24 hours
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 20 mL of a tetrahydrofuran solution of 2.88 g of ethynylnaphthalene was added 25 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 −90° C., and then 12 mL of a tetrahydrofuran solution of 2.3 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., 6.90 g of bromooctadecane was dropped to the resulting solution, and stirred overnight at 30° C. 100 mL of water was dropped to the resulting solution at 0° C., and hexane was added thereto to extract the generated compound. The hexane layer was washed with 30 mL of distilled water for 3 times, dried over anhydrous magnesium sulfate for 24 hours, followed by filtration, and the solvent was removed by evaporation. The resulting product was purified on a column by using hexane as a developing solvent, thereby 1.5 g of 1-ethynyl-2-n-octadecylnaphthalene 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 (32H), 0.9 (3H).

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