Dibenzofuran → HCID 90094861, compound

Participants

Reaction Steps

The title compound was prepared according to General Procedure by heating dibenzofuran (1, 840 mg, 5.0 mmol, 1 equiv.) with KOt-Bu (1.12 g, 10 mmol, 2 equiv.) and Et3SiH (4.0 ml, 25 mmol, 5 equiv.) in 20 ml of toluene for 20 hours at 100° C. After acidic aqueous work up, the crude reaction mixture was purified by chromatography on silica using hexanes and hexanes-ether (10:1) to give, among other isolated products, 20 mg (0.05 mmol, 1%) of 7. Data for (7): oily solid 1H-NMR (300 MHz, CDCl3): δ 7.53-7.44 (m, 2Har), 7.46-7.44 (m, 2Har), 7.36 (dd, J=1.5, 7.5 Hz, 1Har), 7.23 (dd, J=1.5, 7.5 Hz, 1Har), 6.98 (t, J=7 Hz, 1Har), 5.42 (s, 1H, OH), 1.01-0.96 (m, 18H, 6CH3) 0.91-0.77 (m, 15H, 6CH2). 13C NMR (75 MHz, CDCl3): δ 157.37, 139.45, 136.61, 135.87, 135.09, 133.86, 131.38, 129.57, 128.71, 127.55, 122.97, 120.36, 7.80, 7.57, 3.69, 3.46. HRMS: [C24H38OSi2] calculated 398.2461; measured 396.2470.

Provenance & Evidence