Ethanol → HCID 53356868, compound

Participants

Reaction Conditions

Reaction Steps

6,7-Dichloro-2-methyl-9-tosyl-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.13 g, 0.26 mmol) was dissolved in THF (10 mL) and KOH (0.070 g, 1 mmol) in water (10 mL) was added followed by EtOH (3 mL). The reaction mixture was heated to 60° C. for 4 h, diluted with water (10 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by column chromatography [EtOAc-hexane (1:4) as eluant] to give the title compound (0.025 g, 28%) 1H NMR (500 MHz, CDCl3, δ in ppm) (mixture of two diastereomers) 8.22 (br s, 1H), 8.15 (bs, 1H), 7.60 (s, 1H), 7.47 (s, 1H), 2.82-2.63 (m, 2H), 2.51 (s, 1H), 2.46-2.43 (m, 1H), 2.33 (s, 1H), 2.28 (s, 1H), 2.14-2.10 (m, 2H), 2.03-1.98 (m, 1H), 1.82-1.79 (m, 1H), 1.22-1.20 (m, 3H).

Provenance & Evidence