Reaktion #79380

Reaktionsgleichung

tributyl tin chloride

butyl lithium

hexane

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

→

oil

Ausbeute 98.1%

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

Ausbeute 98.1%

Lösungsmittel

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to 0°
2. 2
   ExtraktionThe product was extracted into ether (3×100 ml)
3. 3
   TrocknenThe combined organic extracts were dried (MgSO4)
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue was triturated with isohexane (3×100 ml)
6. 6
   Sonstigethe mother liquors were decanted
7. 7
   Einengenconcentrated

Vorschrift

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.

Quelle