Reacción #88930

Ecuación de reacción

chlorotriisopropylsilane

methyl 5-iodosalicylate

imidazole

→

title compound

Rendimiento 92.1%

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

Rendimiento 92.1%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was evaporated in vacuo
2. 2
   Otrothe residue was partitioned between EtOAc and water
3. 3
   ExtracciónThe aqueous layer was then extracted with EtOAc (2×)
4. 4
   LavadoThe combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine
5. 5
   Secadodried (Na2SO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated in vacuo
8. 8
   OtroThe residue was purified by FCC

Procedimiento

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+].

Fuente