Potassium Hydroxide → HCID 53356845, compound

Participants

Reaction Steps

To 6,7-dichloro-2-fluoro-9-tosyl-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.2 g, 0.35 mmol) in THF (10 mL), KOH (98 mg, 1.7 mmol) in H2O (10 mL) was added and the resulting mixture was refluxed for 6 h. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3×30 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography [EtOAc-hexane (1:9) as eluant] and the solid obtained was washed with cold pentane to give the title compound (58 mg, 40%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.25 (bs, 1H), 7.62 (s, 1H), 7.5 (s, 1H), 5.25-5.14 (m, 1H), 3.25 (d, J=6.5 Hz, 1H), 2.94-2.89 (m, 1H), 2.80-2.74 (m, 1H), 2.44-2.39 (m, 1H), 2.35-2.29 (m, 1H).

Provenance & Evidence