Reaktion #88930

Reaktionsgleichung

chlorotriisopropylsilane

methyl 5-iodosalicylate

imidazole

→

title compound

Ausbeute 92.1%

5-Iodo-2-triisopropylsilanyloxy-benzoic acid methyl ester

Ausbeute 92.1%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was evaporated in vacuo
2. 2
   Sonstigethe residue was partitioned between EtOAc and water
3. 3
   ExtraktionThe aqueous layer was then extracted with EtOAc (2×)
4. 4
   WaschenThe combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated in vacuo
8. 8
   SonstigeThe residue was purified by FCC

Vorschrift

A solution of methyl 5-iodosalicylate (2.00 g, 7.20 mmol) in DMF (20 mL) was treated with imidazole (1.22 g, 18.0 mmol) then chlorotriisopropylsilane (1.85 mL, 8.60 mmol). The mixture was stirred at RT for 18 h. The mixture was evaporated in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (2×). The combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-10% EtOAc in cyclohexane, to give the title compound as a colorless oil (2.88 g, 92%). LCMS (Method 3): Rt 5.72 min, m/z 435 [MH+].

Quelle