Réaction #2697

Équation de réaction

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

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autreusing deoxygenated solvents
2. 2
   TempératureThe mixture was cooled on an ice-bath
3. 3
   workup.WAITAfter another 15 min
4. 4
   Autrethe reaction mixture was quenched with dietyl ether/aq
5. 5
   ExtractionNaHCO3, the aqueous layer was extracted with ether
6. 6
   Lavagethe combined organic layers were washed with water
7. 7
   Séchagedried (Na2SO4)
8. 8
   AutreAfter evaporation and chromatography (silica gel, chloroform) essentially pure product (6.3 g, 92%)
9. 9
   Autrecould be collected

Mode opératoire

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.

Source