反応 #88930

反応方程式

chlorotriisopropylsilane

methyl 5-iodosalicylate

imidazole

→

title compound

収率 92.1%

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

収率 92.1%

溶媒

DMF

反応条件

後処理

1. 1
   その他The mixture was evaporated in vacuo
2. 2
   その他the residue was partitioned between EtOAc and water
3. 3
   抽出The aqueous layer was then extracted with EtOAc (2×)
4. 4
   洗浄The combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine
5. 5
   乾燥dried (Na2SO4)
6. 6
   ろ過filtered
7. 7
   その他evaporated in vacuo
8. 8
   その他The residue was purified by FCC

実験手順

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+].

出典