Реакция #5702

Уравнение реакции

ethyl chloroformate

ethyl α-[3(trifluoromethyl)-benzylamino]-indole-3-acetate

sodium hydride

→

title compound

Выход 66.4%

Ethyl α-[3(trifluoromethyl)-benzylamino]-1-ethoxycarbonyl-indole-3-acetate hydrochloride

Выход 66.4%

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for two hours at room temperature
3. 3
   ДругоеAt the end of this time, the reaction contents
4. 4
   Экстракцияthe aqueous solution extracted with ether
5. 5
   Промывкаthe ether solution washed with saturated brine
6. 6
   Сушкаdried over anhydrous Na2SO4
7. 7
   ДругоеRemoval of the solvent in vacuo
8. 8
   Другоеgave the crude product which
9. 9
   Другоеwas chromatographed with 80 g of silica gel

Методика

To a magnetically stirred solution of ethyl α-[3(trifluoromethyl)-benzylamino]-indole-3-acetate (1.00 g, 2.66 mmol) in 15 mL of DMF was added under nitrogen 0.112 g (2.79 mmol) of sodium hydride (60% oil dispersion). After stirring at room temperature for 10 minutes, 0.26 ml (2.79 mmol) of ethyl chloroformate was added. Stirring was continued for two hours at room temperature. At the end of this time, the reaction contents were poured into ice water, the aqueous solution extracted with ether and the ether solution washed with saturated brine and dried over anhydrous Na2SO4. Removal of the solvent in vacuo gave the crude product which was chromatographed with 80 g of silica gel using hexane-ethyl acetate (4:1) to yield 0.857 g of the title compound.

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