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7473
4.2.12. 3-Benzyl-4-hydroxy-2H-chromen-2-one (14)
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H5
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H6
H7
O
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H8
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4-Hydroxy coumarin (0.162 g, 1.0 mmol), [Cp IrCl2]2 (0.020 g,
*
2.5 mol %), KOH (0.011 g, 0.2 mmol) and benzyl alcohol (1.08 g,
10.0 mmol) were combined in a thick walled glass tube. The tube
was sealed with a rubber septum and purged with nitrogen. The
reaction mixture was heated with stirring at 110 ꢀC for 48 h.
Chromatography eluting with 1:99 v/v methanol and DCM gave the
product (0.219 g, 87%) as a colourless solid. Mp 207.0–208.0 ꢀC (lit.
Mp 207.0–209.0 ꢀC);35 dH (500 MHz, CDCl3); 7.74 (dd, 1H, J 1.3, 8.1,
H5), 7.54 (ddd,1H, J 1.3, 7.3, 8.5, H7), 7.37–7.33 (m, 5H, 5ꢁArH), 7.31–
7.27 (m, 2H, 2ꢁArH), 6.12 (br s,1H, OH), 4.04 (s, 2H, CH2); nmax/cmꢂ1
(solid) 1662, 1614, 1567, 1494, 1392, 1185, 1108, 750; HRMS [ESþ]
found MþNa, 275.0679. C16H12O3Na requires 275.0679.
4.2.13. 3-Benzylquinolin-4(1H)-one (15)
H5
O
H6
19. Patman, R. L.; Williams, V. M.; Bower, J. F.; Krische, M. J. Angew. Chem., Int. Ed.
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H7
20. Patman, R. L.; Chaulagin, M. R,; Williams, V. M.; Krische, M. J. J. Am. Chem. Soc.
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H2
N
H
H8
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ture was allowed to cool. Chromatography eluting with 3:97 v/v
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219.0 ꢀC; dH (500 MHz, DMSO-d6); 11.69 (br s, 1H, NH), 8.12 (d, 1H, J
7.7, H5), 7.86 (s, 1H, H2), 7.62 (appar t, 1H, J 7.7, H6), 7.52 (d, 1H, J 8.3,
H8), 7.32–7.23 (m, 4H, 4ꢁArH), 7.15 (appar t, 1H, J 7.5, H7), 3.78 (s,
2H, CH2); dC (75 MHz, DMSO-d6); 176.25 (CO), 141.72 (ArC), 140.01
(ArC), 137.81 (ArCH), 131.60 (ArCH), 128.90 (2ꢁArCH), 128.43
(2ꢁArCH), 125.96 (ArCH), 125.44 (ArCH), 125.05 (ArC), 123.08
(ArCH), 120.74 (ArC), 118.43 (ArCH), 33.32 (CH2); nmax/cmꢂ1 (solid)
1629, 1549, 1526, 1474, 1455, 1367, 1208, 761; HRMS [ESþ] found
Mþ1, 236.1079. C16H14NO requires 236.1070.
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Acknowledgements
We thank Leeds University, Pfizer and Johnson Matthey for
support.
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