반응 #955951

반응 방정식

4

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

KF

→

5,5′-diethynyl-2,2′-bipyridine

용매

MeOH

THF

반응 조건

후처리

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

실험 절차

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).

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