반응 #2697

반응 방정식

2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole

n-butyllithium

chlorotrimethylsilane

→

8-Trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole

용매

THF

반응 조건

후처리

1. 1
   기타using deoxygenated solvents
2. 2
   온도The mixture was cooled on an ice-bath
3. 3
   workup.WAITAfter another 15 min
4. 4
   기타the reaction mixture was quenched with dietyl ether/aq
5. 5
   추출NaHCO3, the aqueous layer was extracted with ether
6. 6
   세척the combined organic layers were washed with water
7. 7
   건조dried (Na2SO4)
8. 8
   기타After evaporation and chromatography (silica gel, chloroform) essentially pure product (6.3 g, 92%)
9. 9
   기타could be collected

실험 절차

The reaction was performed under an argon atmosphere using deoxygenated solvents. 2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole (6.0 g, 23.6 mmol) was dissolved in dry THF (120 mL). The mixture was cooled on an ice-bath and n-butyllithium (10.8 mL, 2.5M in hexane) was added dropwise over 10 min. After 15 min, chlorotrimethylsilane (6.0 mL, 47.2 mmol) was added dropwise over 5 min. After another 15 min, the reaction mixture was quenched with dietyl ether/aq. NaHCO3, the aqueous layer was extracted with ether and the combined organic layers were washed with water and dried (Na2SO4). After evaporation and chromatography (silica gel, chloroform) essentially pure product (6.3 g, 92%) could be collected.

출처