Реакция #1973917

Уравнение реакции

chloromethyl ethyl ether

methyl 1H-indole-4-carboxylate

potassium hexamethyldisilazide

→

title compound

Выход 75.0%

methyl 1-(ethoxymethyl)-1H-indole-4-carboxylate

Выход 75.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONis then added at 0-5° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Другоеquenched carefully with 300 mL of water
4. 4
   Экстракцияextracted with ethyl acetate (EA, 3×300 mL)
5. 5
   ПромывкаThe combined extracts are washed with aqueous saturated sodium chloride (2×400 mL)
6. 6
   Сушкаdried over Na2SO4
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated
9. 9
   ДругоеThe residue is purified by chromatography on silica gel

Методика

Under nitrogen, to a solution of methyl 1H-indole-4-carboxylate (80 g, 0.46 mol) in THF (700 mL) is added potassium hexamethyldisilazide (1 M in THF, 550 mL, 0.55 mol) in drops at 0° C. The mixture is stirred at 0° C. for 30 minutes (min) and chloromethyl ethyl ether (51 mL, 0.55 mol) is then added at 0-5° C. After the addition, the reaction mixture is stirred at ambient temperature for another 3 hours (h), quenched carefully with 300 mL of water and extracted with ethyl acetate (EA, 3×300 mL). The combined extracts are washed with aqueous saturated sodium chloride (2×400 mL), then dried over Na2SO4, filtered and concentrated. The residue is purified by chromatography on silica gel to give the title compound (80 g, 75%). MS (m/z): 234 (M+H)+.

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