ChemicalBook CAS DataBase List DA-6034

DA-6034 synthesis

6synthesis methods

Product Name:DA-6034
CAS Number:203191-10-0
Molecular formula:C20H18O8
Molecular Weight:386.35

Acetic acid, 2-[[2-(3,4-dimethoxyphenyl)-5-methoxy-4-oxo-4H-1-benzopyran-7-yl]oxy]-, ethyl ester

847909-46-0
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203191-10-0
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Yield:203191-10-0 99%

Reaction Conditions:

Stage #1: 7-ethyloxycarbonylmethyloxy-3',4',5-trimethoxy flavonewith sodium hydroxide in tetrahydrofuran;water; for 2 h;Heating / reflux;
Stage #2: with hydrogenchloride in water at 0 - 5;

Steps:

2.4

165 g of the compound prepared in the above step 3 was dissolved in 800 MT of tetrahydrofuran. To the reaction solution was added 800 mg of 1 N sodium hydroxide solution, and heated to reflux for 2 hours. The reaction solution was cooled down to room temperature, and then ethyl acetate was added to the reaction solution and the organic layer was removed. The obtained water layer was washed with ethyl acetate, and acidified with 1 N hydrochloric acid aqueous solution at 0 ~ 5C. The produced crystals were filtered and dried, followed by washing with water and acetone. The washed crystals were dried again and added to 8 L of a mixed solution of chloroform and methanol (3: 1 v/v), followed by stirring at room temperature for 3 hours. The washing processes were repeated once again and dried to give a target compound (152 g, yield 99%). 1H NMR (DMSO-d6, 400ME 3. 82 (s, 3H), 3.83 (s, 3H), 3.86 (s, 3H), 4.85 (s, 2H), 6.52 (d, 1H), 6.77 (s, 1H), 6.85 (D, 1H), 7.08 (d, 1H), 7.50 (d, 1H), 7.65 (dd, 1H), 13.15 (br s, 1H)

References:

WO2005/23244,2005,A1 Location in patent:Page/Page column 32-33

Acetic acid, 2-[[2-(3,4-dimethoxyphenyl)-5-methoxy-4-oxo-4H-1-benzopyran-7-yl]oxy]-, 1,1-dimethylethyl ester

847909-43-7
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203191-10-0
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References

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one

1174162-87-8
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203191-10-0
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References

4712-12-3
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Acetic acid, 2-[[2-(3,4-dimethoxyphenyl)-5-hydroxy-4-oxo-4H-1-benzopyran-7-yl]oxy]-, ethyl ester

847909-45-9
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203191-10-0
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References