Reaktion #91519

Reaktionsgleichung

(1-(phenylsulfonyl)-2-(1-(phenylsulfonyl)-1H-indol-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

sodium hydroxide

→

(2-(1H-indol-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

Ausbeute 60.0%

Lösungsmittel

ethanol

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder refluxing condition in darkness
2. 2
   Extraktionextracted by ethyl acetate (200 mL)
3. 3
   TrocknenThe organic layer was dried over magnesium sulfate
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified by flash column chromatography (hexane:ethyl acetate 1:1)
6. 6
   Sonstigeto give a yellow solid

Vorschrift

To a solution of (1-(phenylsulfonyl)-2-(1-(phenylsulfonyl)-1H-indol-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone (17yaa) (1 mmol) in ethanol (40 mL) and water (4 mL) was added sodium hydroxide (10 equiv, 10 mmol) and stirred overnight under refluxing condition in darkness. The reaction mixture was diluted by 50 mL of water and extracted by ethyl acetate (200 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (hexane:ethyl acetate 1:1) to give a yellow solid. Yield: 60%. 1H NMR (500 MHz, CD3OD) δ 8.31 (d, J=6.5 Hz, 1H), 7.99 (s, 1H), 7.90 (s, 1H), 7.48-7.52 (m, 3H), 7.24-7.28 (m, 2H), 4.00 (s, 6H), 3.93 (s, 3H). MS (ESI) calcd for C21H19N3O4 377.1. found 400.1 [M+Na]+. Mp 208-210° C.

Quelle