Reaction #955951

Reaction equation

4

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

KF

→

5,5′-diethynyl-2,2′-bipyridine

Solvents

MeOH

THF

Conditions

Workup

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

Procedure

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).

Source