반응 #554605

반응 방정식

lithium hydroxide trihydrate

ethanol

ethyl acetate

Ethyl 4,6-dibromo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate

→

3-(2-Carboxyethyl)-4,6-dibromo-1H-indole-2-carboxylic acid

수율 95.0%

용매

hexane

THF

water

methanol

—

petrol ether

water

tetrahydrofurane

반응 조건

후처리

1. 1
   workup.STIRRINGto stir at rt for 24 h
2. 2
   기타was removed under reduced pressure
3. 3
   추출the product was extracted with diethyl ether (3×30 ml)
4. 4
   건조The organic layers were dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   기타evaporated to dryness
7. 7
   기타to yield a light-beige-colored solid in 95-100% yield

실험 절차

Ethyl 4,6-dibromo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate (4.47 g, 10 mmol) was dissolved in 25 ml tetrahydrofurane (THF) with stirring at rt. Then a solution of 1.26 g of lithium hydroxide trihydrate (3 equiv.) in 25 ml water was added and the resulting mixture was let to stir at rt for 24 h. After completion of the reaction THF was removed under reduced pressure and the pH was adjusted to 4-5, and the product was extracted with diethyl ether (3×30 ml). The organic layers were dried over magnesium sulfate, filtered, and evaporated to dryness to yield a light-beige-colored solid in 95-100% yield. mp. 259° C.; well soluble in methanol, ethanol and ethyl acetate; slightly soluble in petrol ether, water, hexane. 1H-NMR (MeOH-d4): δ 2.67 (t, 2H, 3J=8.4 Hz, CH2); 3.71 (t, 2H, 3J=8.4 Hz, CH2); 7.42 (d, 1H, 4J=1.6 Hz, C7-H); 7.62 (d, 1H, 4J=1.6 Hz, C5-H). 13C-NMR (MeOH-d4): δ 21.4 (C-2′); 37.9 (C-1′); 115.9 (C-7); 117.0 (C-4); 118.8 (C-6); 123.9 (C-3); 125.5 (C-2); 127.9 (C-3a); 128.2 (C-5); 139.6 (C-7a); 164.6 (2′-CO2H); 170.1 (2-CO2H). LC-MS (m/z): 392.0 [M]+; 390.0 [M]−. Purity (LC-MS): 99%.

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