Réaction #6921

Équation de réaction

tributyl tin chloride

butyl lithium

hexane

2-Bromo-4-(1,3-dioxolan-2-yl) thiazole

→

oil

Rendement 98.1%

4-(1,3-Dioxolan-2-yl)-5-(tributylstannyl)thiazole

Rendement 98.1%

Solvants

water

THF

Conditions de réaction

Traitement

1. 1
   Températureto warm to 0°
2. 2
   ExtractionThe product was extracted into ether (3×100 ml)
3. 3
   SéchageThe combined organic extracts were dried (MgSO4 )
4. 4
   Autreevaporated
5. 5
   AutreThe residue was triturated with isohexane (3×100 ml)
6. 6
   Autrethe mother liquors were decanted
7. 7
   Concentrationconcentrated

Mode opératoire

2-Bromo-4-(1,3-dioxolan-2-yl) thiazole (6.4 g ,27.14 mmol) was stirred at −78° C. in dry THF (38 ml). 1.6M n butyl lithium in hexane (18.6 ml, 29.78 mmol) was added dropwise under nitrogen. After 30 min at this temperature, tributyl tin chloride (7.35 ml, 27.14 mmol) was added dropwise. The reaction was allowed to warm to 0° and water (20 ml) was added. The product was extracted into ether (3×100 ml). The combined organic extracts were dried (MgSO4 ) and evaporated. The residue was triturated with isohexane (3×100 ml) and the mother liquors were decanted, combined and concentrated to give a brown oil (11.88 g); m/z 444–450.

Source