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ChemicalBook CAS DataBase List AYANIN
572-32-7

AYANIN synthesis

13synthesis methods
-

Yield: 28% ， 60%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 25; for 12 h;Inert atmosphere;regioselective reaction;

Steps:

3.1.29. Synthesis of dimethylether 25 and trimethylether 31
To a solution of 1 (151 mg, 0.5 mmol) in dry DMF (20 ml) was added K2CO3 (276 mg, 2.0 mmol, 4.0 equiv.) and iodomethane (0.11 ml, 1.75 mmol, 3.5 equiv.) at room temperature. After 12 h, the reaction mixture was then partitioned between 100 ml ethyl acetate and 100 ml water. The ethyl acetate layer was then washed with brine (100 ml), dried over MgSO4, filtered and concentrated. The crude material was purified by column chromatography (25% ethyl acetate in petroleum ether) to yield 25 (46 mg, 28% yield) and 31 (103 mg, 60% yield) as yellow solids.3.1.30. 3,5-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-4H-chromen-4-one (25)Mp 185-186 °C. 1H NMR (CDCl3, 300 MHz) δ 3.86 (s, 3H, -OCH3), 3.98 (s, 3H, -OCH3), 5.70 (s, 1H, 3'-OH), 6.28 (d, J = 2.0 Hz, 1H, 6-H), 6.41 (d, J = 2.0 Hz, 1H, 8-H), 6.98 (d, J = 8.6 Hz, 1H, 5'-H), 7.68 (d, J = 2.0 Hz, 1H, 2'-H), 7.78 (dd, J = 2.0, 8.6 Hz, 1H, 6'-H), 12.68 (s, 1H, 5-OH). ESI-MS m/z: 331 [M + H]+, 353 [M + Na]+.3.1.31. 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one (31)Mp 148-149 °C. 1H NMR (CDCl3, 300 MHz) δ 3.87 (s, 6H, -OCH3), 3.99 (s, 3H, -OCH3), 5.70 (s, 1H, -OH), 6.35 (d, J = 2.2 Hz, 1H, 6-H), 6.44 (d, J = 2.2 Hz, 1H, 8-H), 6.96 (d, J = 8.6 Hz, 1H, 5'-H), 7.69 (d, J = 2.0 Hz, 1H, 2'-H), 7.78 (dd, J = 2.0, 8.6 Hz, 1H, 6'-H), 12.63 (s, 1H, 5-OH). ESI-MS m/z: 345 [M + H]+, 367 [M + Na]+.

References:

Shi, Zhi-Hao;Li, Nian-Guang;Tang, Yu-Ping;Wei-Li;Lian-Yin;Yang, Jian-Ping;Hao-Tang;Duan, Jin-Ao [European Journal of Medicinal Chemistry,2012,vol. 54,p. 210 - 222] Location in patent:experimental part

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