Toluene → Ethyl 1-(4-methoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylate
Reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([CH3:18])=[C:16]([C:19]([OH:21])=[O:20])[CH:15]=[N:14]2)=[CH:9][CH:8]=1.[C:22]1(C)C=CC=C[CH:23]=1>>[CH2:22]([O:20][C:19]([C:16]1[CH:15]=[N:14][N:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:12][CH:11]=2)[C:17]=1[CH3:18])=[O:21])[CH3:23]Participants
Conditions
- Temperature
- 80 °C
Procedure
Thionyl chloride (3.84 g) was added to a solution of 1-(4-methoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid (5.0 g) described in Reference Example 5 in toluene (20 ml) at room temperature, stirred at 80° C. for an hour and the solvent and an excess amount of thionyl chloride were evaporated. Pyridine (10 ml) and ethanol (20 ml) were added to the resulting residue and stirred at 40° C. for 0.5 hour. After completion of the reaction, the solvent was evaporated and ethyl acetate and 1N aqueous solution of sodium hydroxide were added. The mixture was extracted with ethyl acetate three times and the organic layer was dried over anhydrous sodium sulfate and concentrated to give 1-(4-methoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (5.2 g).
Workup
- customthe solvent and an excess amount of thionyl chloride were evaporated
- additionPyridine (10 ml) and ethanol (20 ml) were added to the resulting residue
- stirringstirred at 40° C. for 0.5 hour
- customAfter completion of the reaction
- customthe solvent was evaporated
- additionethyl acetate and 1N aqueous solution of sodium hydroxide were added
- extractionThe mixture was extracted with ethyl acetate three times
- dry with materialthe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cc9c83ffea4949508ec6cb4c2ace485e
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150555B2
Reaction notes
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