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7,4'-Dibenzyl Daidzein synthesis

5synthesis methods
-

Yield:1179998-29-8 79%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 40; for 2 h;

Steps:

7-Benzyloxy-3-(4-benzyloxyphenyl)chrome-4-one 3

Compound 2 (540.8 mg, 2.11 mmol) was dissolved in dryDMF (2 mL), and K2CO3 (961.8 mg, 6.38 mmol) and benzylbromide (1113.4 mg, 6.38 mmol) were added. The mixture washeated at 40 °C for 2 h. After cooling the mixture to roomtemperature, ethyl acetate and water were added. The organiclayer was washed several times with water and brine, andthen dried over MgSO4. The residue was purified by silicagel column chromatography (eluent; n-hexane/EtOAc = 4 : 1)to afford compound 3 (743.2 mg, 1.70 mmol, 79%) as a yellowsolid. Rf = 0.27 (n-hexane/EtOAc = 4 : 1); 1H-NMR (400 MHz,CDCl3) δ: 8.22 (1H, d, J = 9.2 Hz), 7.91 (1H, s), 7.50-7.33 (10H, m), 7.07-7.03 (3H, m), 6.93 (1H, s), 5.18 (2H, s), 5.11 (2H,s); 13C-NMR (100 MHz, CDCl3) δ: 175.8, 162.9, 152.1, 135.7,130.1, 128.8, 128.6, 128.4, 127.9, 127.5, 127.4, 115.0, 114.9,105.0, 101.3, 70.5, 70.1.

References:

Cho, Hye Won;Gim, Hyo Jin;Li, Hua;Subedi, Lalita;Kim, Sun Yeou;Ryu, Jae-Ha;Jeon, Raok [Chemical and Pharmaceutical Bulletin,2021,vol. 69,# 1,p. 99 - 105]