تفاعل #88930

معادلة التفاعل

chlorotriisopropylsilane

methyl 5-iodosalicylate

imidazole

→

title compound

المردود 92.1%

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

المردود 92.1%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was evaporated in vacuo
2. 2
   أخرىthe residue was partitioned between EtOAc and water
3. 3
   استخلاصThe aqueous layer was then extracted with EtOAc (2×)
4. 4
   غسيلThe combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine
5. 5
   تجفيفdried (Na2SO4)
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated in vacuo
8. 8
   أخرىThe residue was purified by FCC

الإجراء التجريبي

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+].

المصدر