1-Bromodecane → 2-Decyl-1-ethynylnaphthalene

Temperature

-80 °C

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).

1. temperaturethe temperature was raised up to 5° C
2. stirringstirred at 20° C. for 2 hours
3. extractionto extract the generated compound
4. washThe diethyl ether layer was washed with 50 mL of distilled water for 3 times
5. dry with materialdried over anhydrous magnesium sulfate for 1 hour
6. filtrationfollowed by filtration
7. customthe solvent was removed by evaporation
8. customThe resulting product was purified on a column

ORD record

ord-fbbf4ccefada495b8890550d7e2d7558

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07715083B2