Réaction #554611

Équation de réaction

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

lithium hydroxide trihydrate

→

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

Rendement 95.0%

Solvants

tetrahydrofurane

water

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGto stir at rt for 24 h
2. 2
   Autrewas removed under reduced pressure
3. 3
   Extractionthe product was extracted with diethyl ether (3×25 ml)
4. 4
   SéchageThe organic layers were dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated to dryness
7. 7
   Autreto yield a light-beige-colored solid in 95-100% yield

Mode opératoire

Ethyl 4,6-diphenyl-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate (4.42 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 (3×25 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. 243-245° C. 1H-NMR (DMSO-d6) δ 2.07 (m, 2H, 2′-H); 2.83 (m, 2H, 1′-H); 7.09 (d, 1H, 2J=1.6 Hz, 7-H); 7.34 (t, 1H, 3J=7.4 Hz, ph-ring), 7.44 (m, 7H, Ph-ring), 7.66 (d, 2H, 2J=0.9 Hz, 5-H); 7.68 (d, 1H, 1.6 Hz, Ph-ring); 11.72 (s, 1H, NH); 12.33 (b, 2H, 2CO2H). 13C-NMR (DMSO-d6) δ 20.3 (C-2′); 34.9 (C-1′); 109.5 (C-4); 120.9 (C-6); 121.7 (C-3); 123.8 (C-2); 125.5 (C-3a); 127.0 (C-2″, C-6″); 127.3 (C-4″′); 127.5 (C-4″); 128.0 (C-3″′, C-5″′); 129.0 (C-3″, C-5″); 129.1 (C-2″′, C-6″′); 135.4 (C-7a); 137.3 (C-4), 137.4 (C-6); 140.8 (C-1″); 141.0 (C-1″′); 163.1 (2′-CO2H); 173.4 (2-CO2H). LC-MS (m/z): 386 [M-NH4+]+, 366 [M]+, 384 [M]−. Purity (LC-MS): 95%.

Source