Potassium Hydroxide → HCID 52946488, compound

Participants

Reaction Steps

2,4-Dichloro-6-(trifluoromethyl)-6-(trimethylsilyloxy)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole (0.3 g, 7.0 mmol) was dissolved in THF (5 mL) and KOH (0.2 g, 3.6 mmol) in water (5 mL) was added to the mixture. The reaction mixture was refluxed for 1 h and then cooled to room temperature, diluted with water and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography [EtOAc-hexane (1:17) as eluant] to furnish the title compound as a pale yellow solid (0.05 g, 21%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.67 (br s, 1H), 7.43 (d, J=1.5 Hz, 1H), 7.41 (d, J=1.5 Hz, 1H), 2.9 (m, 1H), 2.73 (m, 1H), 2.49 (s, 1H) 2.43-2.4 (m, 1H), 2.08-2.03 (m, 4H), 1.16-1.54 (m, 1H)

Provenance & Evidence