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methyl 5-formyl-1-isopropyl-1H-pyrazole-3-carboxylate synthesis

6synthesis methods
1H-Pyrazole-3-carboxylic acid, 5-(hydroxymethyl)-1-(1-methylethyl)-, methyl ester

617709-77-0
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methyl 5-formyl-1-isopropyl-1H-pyrazole-3-carboxylate

617709-79-2
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Yield:617709-79-2 81%

Reaction Conditions:

with magnesium sulfate;pyridinium chlorochromate in dichloromethane at 0 - 20; for 3 h;

Steps:

Methyl 5-formyl-l-(propan-2-yl)-lH-pyrazole-3-carboxylate (Compound INT- 028)

To a suspension of PCC (1.2 g, 5.57 mmol) and magnesium sulfate (1.8 g, 15.0 mmol) in dichloromethane (10 mL) was added a solution of Compound 9c (500 mg, 2.52 mmol) in dichloromethane (5 mL) dropwise at 0°C. The mixture was stirred for 3 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :4). This resulted in 400 mg (81%) of the title compound as a white solid. LC-MS (ESI, m/z): [M+H]+= 197.2.

References:

WO2018/75207,2018,A1 Location in patent:Paragraph 0138; 0141