Acetic Acid → 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxylic acid
Reaction equation
O.[OH-].[Li+].[CH2:4]([N:7]1[C:11]([CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10][C:9]([C:19]([O:21]CC)=[O:20])=[N:8]1)[CH2:5][CH3:6].C(O)(=O)C>CO.O>[CH2:4]([N:7]1[C:11]([CH2:12][CH:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:10][C:9]([C:19]([OH:21])=[O:20])=[N:8]1)[CH2:5][CH3:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Lithium hydroxide monohydrate (3.8 g, 92 mmol) was added to a solution of ethyl 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxylate (6.43 g, 22.9 mmol) in methanol (30 mL) and water (10 mL). The mixture was stirred for 20 hours. Most of the volatiles were removed under reduced pressure, and water (100 mL) and acetic acid (52 mL, 910 mmol) were sequentially added. The solution was cooled to approximately 0° C. After five minutes, a white solid formed, and more water (100 mL) was added. The mixture was stirred for 30 minutes, and the solid was isolated by filtration, washed with water, and dried on the vacuum filter funnel to provide 4.88 g of 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxylic acid as a white solid.
Workup
- additionwere sequentially added
- waitAfter five minutes
- customa white solid formed
- stirringThe mixture was stirred for 30 minutes
- customthe solid was isolated by filtration
- washwashed with water
- customdried on the vacuum
- filtrationfilter funnel
Sources & evidence
- ORD record
- ord-1a26d7dcddc3413c8715a45dbf7d5e64
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943636B2
Reaction notes
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