1-(4-PYRIDINYL)-1,3-BUTANEDIONE synthesis
- Product Name:1-(4-PYRIDINYL)-1,3-BUTANEDIONE
- CAS Number:75055-73-1
- Molecular formula:C9H9NO2
- Molecular Weight:163.17
Yield:75055-73-1 62%
Reaction Conditions:
Stage #1: 4-pyridinecarboxylic acid, methyl ester;propan-2-onewith sodium methoxide in diethyl ether; for 6 h;Heating / reflux;
Stage #2: with lithium hydroxide monohydrate;glacial acetic acid
Steps:
OO-1.1
Stepi: 1-Pyridin-4-ylbutane-1, 3-dione (oo-1); To a 500 mL flask with NaOMe (4.75 g) and anhydrous ether (130 mL) was sequentially added methyl isonicotinate (10.0 mL, 84.7 mmol), and a solution of acetone (12.4 mmol, 169 mmol) in ether {45 mL). The suspension was stirred at reflux for 6 hours, cooled, and filtered. The isolated solid was washed with ether and dissolved in water (40 mL). Glacial acetic acid (5.2 mL) was added and the mixture was extracted with chloroform (40 mL x 2). The organic extracts were dried over anhydrous Na2SO4 and concentrated to give the title compound oo-1 (8.6 g, 62% yield) as a brown solid, which was used without further purification. LCMS: 164.10 [M + H+]
References:
WO2008/17932,2008,A2 Location in patent:Page/Page column 92
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