反応 #955951

反応方程式

4

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

KF

→

5,5′-diethynyl-2,2′-bipyridine

溶媒

MeOH

THF

反応条件

後処理

1. 1
   その他Subsequently, the solvents were removed under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was redissolved in 200 ml CH2Cl2
3. 3
   洗浄washed four times with 100 ml H2O each, in order
4. 4
   その他to remove inorganic salts
5. 5
   乾燥The organic phase was dried over Na2SO4
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他purified by silica flash column chromatography (eluent: CH2Cl2)
8. 8
   その他to yield a colorless powder of 204 mg (1.0 mmol, 81%) pure 5

実験手順

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).

出典