5
18. McLaughlin, M.; Belyk, K. M.; Qian, G.; Reamer, R. A.; Chen,
(2H, d, J 8.0 Hz, arom), 4.81 (2H, s, CH2OH), 3.87 (3H, s,
OCH3), 3.51 (1H, s, OH); δC (50 MHz, CDCl3) 196.7, 164.3,
132.2, 130.0, 114.1, 64.9, 55.5.
ACCEPTED MANUSCRIPT
C.-y. J. Org. Chem. 2012, 77, 5144–5148.
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4.2.12. 1-(4-Chlorophenyl)-2-hydroxyethan-1-one
(21)5 1
Yellowish solid (94% yield); m.p. 117–119 °C (lit. m.p. 116–
118 °C);51 flash column chromatography eluent: PE/AcOEt 8/2 to
7/3 v/v; δH (200 MHz, CDCl3) 7.86 (2H, d, J 6.0 Hz , arom), 7.48
(2H, d, J 6.0 Hz, arom), 4.84 (2H, s, CH2OH), 3.47 (1H, br, OH);
δC (50 MHz, CDCl3) 197.9, 164.3, 132.2, 130.0, 129.7, 65.8.
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4.2.13. Methyl 4-(2-hydroxyacetyl)benzoate (22)3 0
Yellowish solid (96% yield); m.p. 154–156 °C (lit. m.p. 154–
156 °C);32 flash column chromatography eluent: PE/AcOEt 9/1 to
7/3 v/v; δH (200 MHz, CDCl3) 8.16 (2H, d, J 8.0 Hz, arom), 7.97
(2H, d, J 8.0 Hz, arom), 4.86 (2H, s, CH2OH), 3.91 (3H, s,
OCH3), 3.16 (1H, s, OH); δC (50 MHz, CDCl3) 214.5, 139.3,
130.4, 130.1, 127.2, 127.6, 65.8, 52.6; m/z (ESI) 195.1 ([M+H]+,
55%).
4.2.14. 1-(4-Fluorophenyl)-2-hydroxyethan-1-one
(23)1 4
White solid (53% yield); m.p. 108–110 °C (lit. m.p. 109–111
°C);14 flash column chromatography eluent: PE/AcOEt 8/2 to 7/3
v/v; δH (200 MHz, CDCl3) 7.93–7.86 (2H, m, arom), 7.20–7.08
(2H, m, arom) 4.79 (2H, s, CH2OH), 3.47 (1H, br, OH); δC (50
MHz, CDCl3) 196.8, 166.4 (d, JCF 255 Hz), 130.4 (d, JCF 9.5 Hz),
129.8 (d, JCF 3.0 Hz), 116.2 (d, JCF 22 Hz), 65.3.
Acknowledgments
37. Olszewski, T. K.; Jaskólska, D. E. Heteroat. Chem. 2012, 23, 605–
609.
38. Naik, P. U.; Petitjean, L.; Refes, K.; Picquet, M.; Plasseraud, L.
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2014, 79, 2758–2764.
We would like to thank the support of COST action CM0905
“Organocatalysis” and Dr Morgan Hans (University of Liege) for
his help with the synthesis of the precatalysts.
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