Compound 8g
(2-(furan-2-yl)-4-hydroxy-3-methylphenyl)(pyrrolidin-1-yl)methanone
From: Catalytic activation of unstrained C(aryl)–C(aryl) bonds in 2,2′-biphenols
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Compound data: 1H NMR
Compound data: 13C NMR
Compound data: Crystallographic data
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
3ai (20 mg, 0.060 mmol) and tributyl-(2-furyl)stannane (43 mg, 0.120 mmol) were subjected to Method B outlined for compound 8d to give the corresponding phenol 8g as a white solid (13.1 mg, 80% yield). m.p. 242-243 oC. 1H NMR (500 MHz, DMSO-d6) δ 9.77 (s, 1H), 7.71 (d, J = 1.5 Hz, 1H), 6.96 (d, J = 8.5 Hz, 1H), 6.88 (d, J = 8.5 Hz, 1H), 6.54 (dd, J = 3.0, 2.0 Hz, 1H), 6.37 (d, J = 3.0 Hz, 1H), 3.23 (t, J = 7.0 Hz, 2H), 2.88 (t, J = 6.5 Hz, 2H), 2.09 (s, 3H), 1.70 – 1.67 (m, 2H), 1.63 – 1.59 (m, 1H). 13C NMR (126 MHz, DMSO-d6) δ 168.5, 155.6, 150.8, 142.6, 129.8, 128.2, 124.4, 123.1, 114.6, 111.0, 109.6, 47.4, 44.9, 25.3, 24.0, 13.1. HRMS-ESI: [M+H]+ Calculated for C16H18NO3+ 272.1281, Found: 272.1287. IR (film, cm-1) 3140, 2956, 2922, 2871, 2852, 1569, 1448, 1416, 1377, 1289, 1260, 1115.
