Reacción #52306

Ecuación de reacción

n-butyllithium

trimethylsilyl acetylene

tetraethyl orthocarbonate

potassium carbonate

triethoxycarbenium tetrafluoroborate

Boron trifluoride diethyl etherate

→

title compound

Rendimiento 100.0%

Trimethyl-triethoxyprop-1-ynyl-silane

Rendimiento 100.0%

Disolventes

diethyl ether

diethyl ether

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was transferred to a dropping funnel
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.STIRRINGAfter stirring for 1 h at 0° C.
4. 4
   Temperaturathe solution was cooled to −78° C
5. 5
   Otroformed previously
6. 6
   workup.STIRRINGThe mixture was stirred at −78° C. for 1 h
7. 7
   Temperaturabefore being warming to room temperature
8. 8
   Extracciónmixture was extracted with diethyl ether
9. 9
   SecadoThe organic extracts were dried with magnesium sulfate
10. 10
    Otrothe solvent was removed under reduced pressure

Procedimiento

Boron trifluoride diethyl etherate (36.0 mL, 280 mmol) was added to diethyl ether (50 mL) under argon. The mixture was transferred to a dropping funnel and added dropwise under argon to a solution of tetraethyl orthocarbonate (40.0 g, 208 mmol) in diethyl ether (100 mL) at 0° C. After the addition was complete, the mixture was stirred for 5 min and then cooled to −78° C. In a separate reaction flask, n-butyllithium (166 mL, 2.5 M solution in hexanes, 416 mmol) was added dropwise to a solution of trimethylsilyl acetylene (59.0 mL, 416 mmol) in diethyl ether (200 mL) at 0° C. under argon. After stirring for 1 h at 0° C., the solution was cooled to −78° C. This solution was added via cannula to the triethoxycarbenium tetrafluoroborate formed previously. The mixture was stirred at −78° C. for 1 h before being warming to room temperature. Saturated aqueous potassium carbonate was added and mixture was extracted with diethyl ether. The organic extracts were dried with magnesium sulfate and the solvent was removed under reduced pressure to give the title compound (50.0 g, 100% yield) as yellow oil. 1H NMR (CDCl3) δ 3.68(q, 6H, J=7.2 Hz), 1.23 (t, 9H, J=7.2 Hz), 0.20, (s, 9H).

Fuente