Potassium Hydroxide → 6,7-Dichloro-1-(perfluoroethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-ol

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Reaction Steps

To 6,7-Dichloro-1-(perfluoroethyl)-9-tosyl-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.25 g, 0.47 mmol) in THF (5 mL) was added 6N KOH (6 mL). The reaction mixture was stirred at room temperature for 10 min. and then refluxed for 36 h, diluted with water and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by silica gel chromatography [EtOAc-hexane (3:22) as eluant] to give the title compound as a white solid (0.06 g, 34%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.21 (bs, 1H), 7.62 (s, 1H), 7.49 (s, 1H), 2.82-2.80 (m, 1H), 2.68-2.62 (m, 1H), 2.45 (s, 1H), 2.28-2.23 (m, 1H), 2.18-2.15 (m, 1H), 2.12-2.06 (m 1H), 2.03-2.0 (m, 1H).

Provenance & Evidence