ChemicalBook CAS DataBase List SINENSETIN

SINENSETIN synthesis

12synthesis methods

Product Name:SINENSETIN
CAS Number:2306-27-6
Molecular formula:C20H20O7
Molecular Weight:372.37

3535-37-3
208 suppliers
$18.00/1 g

118-41-2 Synthesis

118-41-2
585 suppliers
$14.00/5g

2306-27-6
218 suppliers
$29.00/5mg

Yield:2306-27-6 81%

Reaction Conditions:

Stage #1:3,4-dimethoxybenzoic acid chloride;Eudesmic acid with triethylamine in dichloromethane at 0 - 20; for 2 h;
Stage #2: with trimethylsilyl trifluoromethanesulfonate;triethylamine in dichloromethane at 95; for 2 h;

Steps:

2.2
2,3,4-trimethoxy-6-hydroxyacetophenone, which is compound 13a (904 mg, 4.0 mmol), was added to 16 mL of dichloromethane solution. Triethylamine (1.47 mL, 12 mmol) and 3,4-dimethoxybenzoyl chloride (1.04 g, 5.2 mmol). The reaction system was raised from 0 ° C to room temperature for 2 hours. After the reaction was completed, the system was quenched with water and extracted with ethyl acetate three times. It was washed with saturated brine and dried over anhydrous sodium sulfate. Purification by silica gel column chromatography (petroleum ether / ethyl acetate = 5: 1) to obtain the product 2-acetyl-3,4,5-trimethoxy-3,4-dimethoxy-benzoic acid methyl ester (1.3 g, 3.4 mmol), white solid, yield: 85%.
2-Acetyl-3,4,5-trimethoxy-3,4-dimethoxy-benzoic acid methyl ester (1.17 g, 3.0 mmol) was added to 18 mL of dichloroethane solution, and triethylamine (1.2 mL, 9.0 mmol) and trimethylsilyl trifluoromethanesulfonate (3.3 mL, 18 mmol), and stirred at 95 ° C for 2 hours. After the reaction was completed, the reaction mixture was quenched with methanol, and extracted with ethyl acetate three times. It was washed with saturated brine and dried over anhydrous sodium sulfate. Purification by silica gel column chromatography (petroleum ether / ethyl acetate = 2: 1) to obtain the product 2- (3,4-dimethoxyphenyl) -5,6,7-trimethoxy-4H-benzopyran-4-one (905 mg, 2.4 mmol), brown solid, yield: 81%.

References:

Zhiyuan Pharmaceutical (Qingyuan) Co., Ltd.;Wu Deyan;Xie Ying;Zhou Huifang CN110498784, 2019, A Location in patent:Paragraph 0097; 0102-0104

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