C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]=1[Cl:11])=[O:5])C.[OH-].[Li+].O>CO>[Cl:11][C:10]1[N:9]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]5-Chloro-1-(tetrahydro-pyran-4-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (2.194 g (98%), 8.31 mmol) was dissolved in methanol (12.5 mL). Lithium hydroxide (0.274 g, 11.44 mmol) and water (12.5 mL) were added and the mixture was heated at 80° C. for 1 hour. After cooling to room temperature, the mixture was concentrated to remove the methanol. Tetrahydrofuran was added to the residue and removed in vacuo to ensure complete removal of the methanol. The aqueous residue was treated with 6N HCl (1.88 mL) resulting in the precipitation of a thick milky solid. The solid was collected by filtration, washed with water and dried under high vacuum with heat to give 5-chloro-1-(tetrahydro-pyran-4-yl)-1H-pyrazole-4-carboxylic acid (1.900 g, 99%). Mass spectrum: m/z: 231.30 (M+H).
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