4398
T. A. Salama et al. / Tetrahedron Letters 48 (2007) 4395–4398
Eastgate, M. D. J. Am. Chem. Soc. 2005, 127, 3774–3789;
CH2Cl2 at room temperature was added SiCl4 and the
mixture left to stir until TLC showed disappearance of the
starting material. The reaction was then poured onto
water and filtered. The filtrate as well as the precipitate
was extracted with CH2Cl2. The extracts were collected,
dried over MgSO4 and evaporated. The residue was
purified by silica gel column chromatography (pet.
ether–ethyl acetate 10:1 or 20:1) to give pure 2 or 6,
respectively. Ketones 2 are all known compounds,4,5,18
(c) Lee, S. H.; Jang, B.-B.; Kafafi, Z. H. J. Am. Chem. Soc.
2005, 127, 9071–9078; (d) Acocella, M. R.; De Rosa, M.;
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Matsunogo, H.; Ishizuka, T.; Hashimoto, S.; Nakajima,
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B. J.; Mattseon, D. S. Angew. Chem., Int. Ed. 2004, 43,
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1
except for 2e, mp 95 °C; H NMR (200 MHz, CDCl3): d
7.52–7.57 (m, 8H), 7.23–7.43 (m, 10H), 2.14 (s, 3H,
COMe), 1.89 (s, 3H, CH3); 13C NMR (50 MHz, CDCl3): d
205.2, 142.3, 140.1, 137.5, 131.1, 128.2, 127.9, 127.1, 126.7,
58.9, 29.2, 27.1; MS (m/z, %): 333 (M+ꢀCOMe, 100); IR
(KBr plate) m 3025, 2955, 2850, 1700 (CO), 1600 (C@C),
750, 700 cmꢀ1; Anal. Calcd for C28H24O (376.49): C,
89.33; H, 6.43%. Found: C, 89.19; H, 6.51%. a-Aryl
chalcones 6a,b are known17a,b while 6c,d are unknown.
Data for 6c: mp 136–138 °C; 1H NMR (200 MHz,
CDCl3): d 7.74–7.77 (d, J = 8 Hz, 6H), 7.28–7.51 (m,
7H, 6 Ar-H + vinyl H); 13C NMR (50 MHz, CDCl3): d
194.3, 141.1, 137, 135.1, 134.3, 133.2, 131.9, 130.3, 129.8,
128.2, 128.9, 128.3; IR (KBr plate) m 2930, 1654 (CO),
1586 (C@C), 1484, 1397, 1282, 1011, 851, 754, 688; UV
kmax (EtOH 95%) 262 (e 2000), 223, 211 nm; Anal. Calcd
for C21H13Cl3O (387.65): C, 65.06; H, 3.38%. Found: C,
65.14; H, 3.32%.
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16. A typical procedure for reductive coupling of 1 or 5 with
SiCl4/Zn in the ratio 1:4:6 or 1:2:4, respectively: To a
stirring mixture of zinc and carbonyl compound (1 or 5) in