تفاعل #52306

معادلة التفاعل

n-butyllithium

trimethylsilyl acetylene

tetraethyl orthocarbonate

potassium carbonate

triethoxycarbenium tetrafluoroborate

Boron trifluoride diethyl etherate

→

title compound

المردود 100.0%

Trimethyl-triethoxyprop-1-ynyl-silane

المردود 100.0%

المذيبات

diethyl ether

diethyl ether

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   أخرىThe 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
   درجة الحرارةthe solution was cooled to −78° C
5. 5
   أخرىformed previously
6. 6
   workup.STIRRINGThe mixture was stirred at −78° C. for 1 h
7. 7
   درجة الحرارةbefore being warming to room temperature
8. 8
   استخلاصmixture was extracted with diethyl ether
9. 9
   تجفيفThe organic extracts were dried with magnesium sulfate
10. 10
    أخرىthe solvent was removed under reduced pressure

الإجراء التجريبي

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).

المصدر