Formaldehyde → methyl 1-(hydroxymethyl)-1H-pyrazole-4-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][NH:8][CH:9]=1)=[O:4].[CH2:10]=[O:11].C(N(CC)CC)C>CC(C)=O>[OH:11][CH2:10][N:7]1[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:9]=[N:8]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
The mixture of 1.40 g of 4-methoxycarbonyl-1H-pyrazole, 0.37 g of paraformaldehyde and 0.11 g of triethylamine was stirred at 130° C. for 1 hour. 0.74 g of paraformaldehyde and 2 ml of triethylamine were added to the mixture and stirred at 130° C. for 2 hours. After the reaction mixture was cooled to room temperature, acetone was added. After the mixture was filtered, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.38 g of 1-(hydroxymethyl)-4-methoxycarbonyl-1H-pyrazole.
Workup
- stirringstirred at 130° C. for 2 hours
- temperatureAfter the reaction mixture was cooled to room temperature
- filtrationAfter the mixture was filtered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-33722893bd724639b992c6a8f08dda9d
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07541374B2
Reaction notes
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