Potassium Hydroxide → 1-Hydroxy-1-(perfluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile

Participants

Reaction Steps

To a solution of 1-(perfluoroethyl)-9-tosyl-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (180 mg, 0.3 mmol) in THF (5 mL), KOH (90 mg, 1.6 mmol) in H2O (1 mL) was added. The reaction mixture was refluxed for 20 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 residue which was purified by column chromatography [EtOAc-hexane (1:19) as eluant] to afford the title compound as a white solid (40 mg, 40%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.5 (bs, 1H), 7.9 (s, 1H), 7.49 (d, J=7.5 Hz, 1H), 7.44 (d, J=7.5 Hz, 1H), 2.90-2.86 (m, 1H), 2.74-2.56 (m, 1H), 2.56 (s, 1H), 2.33-2.29 (m, 1H), 2.20-2.12 (m, 2H), 2.04-2.03 (m, 1H).

Provenance & Evidence