反応 #2697

反応方程式

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

溶媒

THF

反応条件

後処理

1. 1
   その他using deoxygenated solvents
2. 2
   温度The mixture was cooled on an ice-bath
3. 3
   workup.WAITAfter another 15 min
4. 4
   その他the reaction mixture was quenched with dietyl ether/aq
5. 5
   抽出NaHCO3, the aqueous layer was extracted with ether
6. 6
   洗浄the combined organic layers were washed with water
7. 7
   乾燥dried (Na2SO4)
8. 8
   その他After evaporation and chromatography (silica gel, chloroform) essentially pure product (6.3 g, 92%)
9. 9
   その他could be collected

実験手順

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.

出典