Reacción #2697

Ecuación de reacción

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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrousing deoxygenated solvents
2. 2
   TemperaturaThe mixture was cooled on an ice-bath
3. 3
   workup.WAITAfter another 15 min
4. 4
   Otrothe reaction mixture was quenched with dietyl ether/aq
5. 5
   ExtracciónNaHCO3, the aqueous layer was extracted with ether
6. 6
   Lavadothe combined organic layers were washed with water
7. 7
   Secadodried (Na2SO4)
8. 8
   OtroAfter evaporation and chromatography (silica gel, chloroform) essentially pure product (6.3 g, 92%)
9. 9
   Otrocould be collected

Procedimiento

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.

Fuente