HCID 22405679, compound → HCID 22405678, compound

Participants

Reaction Steps

To a solution of 5-[1,2-dioxo-4-(1-methylethoxy)-3-cyclobuten-3-yl]-3-(3-triisopropylsiloxypropyl)-1-triisopropylsilylindole (11) (0.315 g, 0.50 mmol) in 5 mL of acetonitrile was added 48% HF (10% in MeCN, 0.35 mL, 1.0 mmol) and the mixture was stirred at room temperature for 30 min. The reaction was then quenched with 10% aqueous Na2CO3, ethyl acetate was added and the mixture was washed (10% aq. Na2CO3, brine), dried (Na2SO4) and evaporated to give a yellow gum. Flash chromatography (SiO2 /hexane-ethyl acetate, 1:1) of this gum afforded the title compound (0.209 g, 89%) as a yellow foam: IR (neat) 3480 (br), 1782, 1735, 1585, 1390 cm- ; 1H NMR (CDCl3, 200 MHz) δ 8.43 (d, J=1.4 Hz, 1H), 7.82 (dd, J=8.7, 1.7 Hz, 1H), 7.56 (d, J=8.7 Hz, 1H), 7.10 (s, 1H), 5.64 (hept, J=6.2 Hz, 1H), 3.74 (t, J=6.4 Hz, 2H), 2.90 (t, J=7.4 Hz, 2H), 2.09-1.95 (m, 2H), 1.69 (hept, J=7.5 Hz, 3H), 1.57 (d, J=6.2 Hz, 6H), 1.14 (d, J=7.5 Hz, 18H).

Provenance & Evidence