E
Z. Yin et al.
Letter
Synlett
References and Notes
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(23) General Procedure
To a mixture of aromatic aldehydes (5 mmol) and acetophenone
(11 mmol) a fine powder of NaOH (5 mmol) and K2CO3 (5
mmol) was added. The reaction mixture was ground at room
temperature until it became incompact solid (generally 20–30
min). After the solid was treated with water, the water-insolu-
ble solid was recrystallized in ethanol.
3-(2,6-Dichlorophenyl)-1,5-diphenylpentane-1,5-dione (4a)
Mp 125–128 °C, 86% yield, white solid. 1H NMR (400 MHz,
CDCl3): = 8.03–7.93 (m, 4 H), 7.54 (d, J = 7.4 Hz, 2 H), 7.45 (t, J =
7.6 Hz, 4 H), 7.33 (d, J = 7.9 Hz, 1 H), 7.23 (d, J = 7.9 Hz, 1 H), 7.06
(14) (a) Tzeli, D.; Tsoungas, P. G.; Petsalakis, I. D.; Kozielewicz, P.
Struct. Chem. 2017, 28, 925. (b) Thomas, J.; Liu, X.; Jäger, W.; Xu,
Y. Angew. Chem. Int. Ed. 2015, 54, 11711. (c) Preimesberger, M.
R.; Majumdar, A.; Aksel, T.; Sforza, K.; Lectka, T.; Barrick, D.;
Lecomte, J. T. J. Am. Chem. Soc. 2015, 137, 1008.
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43, 2703.
(t, J = 8.0 Hz, 1 H), 5.07 (p, J = 7.1 Hz, 1 H), 3.84–3.65 (m, 4 H). 13
C
NMR (100 MHz, CDCl3): = 198.3, 138.3, 136.9, 136.7, 134.5,
133.2, 129.9, 128.9, 128.6, 128.3, 128.2, 41.1, 33.3.
Crystal Structure of Compound 4a
C
23H18Cl2O2, MW = 397.27, Dcalc = 1.342 g/cm3; V = 983.0(2) Å3,
(16) (a) Hu, X. Y.; Shan, Z. X.; Soloshonok, V. A. Cryst. Growth Des.
2012, 12, 33. (b) Hu, X. Y.; Guo, J. X.; Yin, Z. Y.; Shan, Z. X. Chem-
istrySelect 2018, 3, 3309.
triclinic; Z = 2; space group P-1, a = 9.4157(12), b = 10.3008(14),
c = 10.9517(15), (Mo K) = 0.345 mm–1, –11 ≤ h ≤ 12, –13 ≤ k ≤
13, –14 ≤ l ≤ 14, F(000) = 412, GOF = 1.059, T = 296 (2) K; CCDC
1904249.
© 2019. Thieme. All rights reserved. Synlett 2019, 30, A–E