1,3-bis(3,4-dimethoxyphenyl)propane-1,3-dione synthesis
- Product Name:1,3-bis(3,4-dimethoxyphenyl)propane-1,3-dione
- CAS Number:52751-63-0
- Molecular formula:C19H20O6
- Molecular Weight:344.36
Yield:52751-63-0 99%
Reaction Conditions:
Stage #1: ethyl veratratewith sodium hydride in tetrahydrofuran;dimethyl sulfoxide at 10 - 15;Inert atmosphere;
Stage #2: 3-(3,4-dimethoxyphenyl)-5-(3-fluorophenyl)isoxazole in tetrahydrofuran;dimethyl sulfoxide at 10 - 20;Inert atmosphere;
Steps:
2.2
A 60% suspension of sodium hydride in mineral oil (0.4 g, 10 mmol) was washed with petroleum benzin (20 ml) two times, anhydrous DMSO (10 ml) was added. After being stirred for 30 min at room temperature under argon, THF (5 ml) was added, the flask was cooled down to 15°C and ethyl 3,4-dimethoxybenzoate (2.1 g, 10 mmol) was added. The temperature was allowed to drop to 100C and a solution of 3,4-dimethoxyacetophenone (1.08 g, 6 mmol) in DMSO (4 ml) was added at such a rate that the temperature didn't rise above 15°C. Upon completion of addition the reaction mixture was stirred 72 h at room temperature, then poured slowly into crushed ice (250 g) containing 85% phosphoric acid (1 ml). Resulting precipitate was collected by filtration, washed with water (50 ml) and dried to provide 5 (2.1 g, 99%) as a yellow powder
References:
WO2010/372,2010,A2 Location in patent:Page/Page column 43-44
3943-77-9
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