Reacción #955951

Ecuación de reacción

4

5,5′-Bis((trimethylsilyl)ethynyl)-2,2′-bipyridine

KF

→

5,5′-diethynyl-2,2′-bipyridine

Disolventes

MeOH

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSubsequently, the solvents were removed under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was redissolved in 200 ml CH2Cl2
3. 3
   Lavadowashed four times with 100 ml H2O each, in order
4. 4
   Otroto remove inorganic salts
5. 5
   SecadoThe organic phase was dried over Na2SO4
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   Otropurified by silica flash column chromatography (eluent: CH2Cl2)
8. 8
   Otroto yield a colorless powder of 204 mg (1.0 mmol, 81%) pure 5

Procedimiento

4 (390 mg, 1.12 mmol) was dissolved in a mixture of 40 ml MeOH and 10 ml THF; then KF powder (400 mg, 6.88 mmol) was added and the solution was stirred at room temperature overnight. Subsequently, the solvents were removed under reduced pressure. The residue was redissolved in 200 ml CH2Cl2 and washed four times with 100 ml H2O each, in order to remove inorganic salts. The organic phase was dried over Na2SO4, concentrated under reduced pressure and purified by silica flash column chromatography (eluent: CH2Cl2) to yield a colorless powder of 204 mg (1.0 mmol, 81%) pure 5. 1H NMR (CDCl3, 250 MHz): δ=8.76 (d, 2H, JHH=1.0 Hz, bpy-H), 8.39 (d, 2H, JHH=6.0 Hz, bpy-H), 7.90 (dd, 2H, JHH=1.1 Hz, 5.1 Hz, bpy-H), 3.31 (s, 2H, bpy-CCH).

Fuente