반응 #88930

반응 방정식

chlorotriisopropylsilane

methyl 5-iodosalicylate

imidazole

→

title compound

수율 92.1%

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

수율 92.1%

용매

DMF

반응 조건

후처리

1. 1
   기타The mixture was evaporated in vacuo
2. 2
   기타the residue was partitioned between EtOAc and water
3. 3
   추출The aqueous layer was then extracted with EtOAc (2×)
4. 4
   세척The combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine
5. 5
   건조dried (Na2SO4)
6. 6
   여과filtered
7. 7
   기타evaporated in vacuo
8. 8
   기타The residue was purified by FCC

실험 절차

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+].

출처