Sodium Carbonate → 9-[3-(1-Adamantyl)-4-benzylphenyl]-6-(2-carboxyphenyl)xanthen-3-one

Participants

Reaction Steps

To a stirred suspension of 1.00 g (2.15 mmol) of 9-(trifluoromethane-sulfonyloxy)-6-(2-carboxyphenyl)xanthen-3-one, 0.80 g (2.20 mmol) of 3-(1-adamantyl)-4-benzyloxyphenylboronic acid [1H NMR (300 MHz, CDCl3) δ 1.77, 2.26 (2 s, 12, AdCH2), 2.07 (s, 3, AdCH), 5.21 (s, 2, CH2), 7.06 (d, J=8.2 Hz, 1, ArH), 7.3–7.5 (m, 5, ArH), 8.03 (d, J=7.8 Hz, 1, ArH), 8.19 ppm (s, 1, ArH)], 0.32 g (0.28 mmol) of Pd[P(C6H5)3]4 and 0.26 g (6.1 mmol) of LiCl in 20 ml of DME was added under Ar 3 ml of 2.0 M aq. Na2CO3. The reaction mixture was heated at reflux (80–85° C.) overnight, at which time the reaction was complete. The mixture was extracted with EtOAc. The extract was washed with brine and water, dried (MgSO4), filtered, and concentrated. Flash column chromatography (10% EtOAc/hexane) yielded a pale red (0.60 g, 44%): Rf0.45 (40% EtOAc/hexane); 1H NMR (400 MHz, CDCl3) δ 1.74, 2.19 (2 s, 12, AdCH2), 2.06 (s, 3, AdCH), 5.17 (s, 2, CH2), 6.55 (dd, J=8.0, 2.0 Hz, 1, ArH), 6.68 (d, J=8.0 Hz, 1, ArH), 6.8–7.7 (m, 16, ArH), 8.05 ppm (d, J=8.0 Hz, 1, ArH).

Provenance & Evidence