Water → 1-Cyclohexyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

HRID 12894Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.O.[OH-].[Li+]>CO>[CH:15]1([N:9]2[C:10]([C:11]([F:12])([F:13])[F:14])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

Cyclohexyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.265 g, 0.91 mmol) was dissolved in methanol (1.4 mL). Water (1.4 mL) and lithium hydroxide (0.029 g, 1.21 mmol) were added and the mixture was heated at 80° C. for 1.5 hours. After cooling to room temperature, the methanol was removed in vacuo. Tetrahydrofuran was added to the residue and then removed in vacuo to ensure complete removal of the methanol. 6N HCl was added to the aqueous residue to pH 2-3, resulting in precipitation of a solid. The solid was collected by filtration, washed with water and dried under high vacuum at 100° C. to give 1-cyclohexyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (0.206 g, 86%). Mass spectrum: m/z: 263.3 (M+H).

Workup

temperatureAfter cooling to room temperature
customthe methanol was removed in vacuo
additionTetrahydrofuran was added to the residue
customremoved in vacuo
customremoval of the methanol
addition6N HCl was added to the aqueous residue to pH 2-3
customresulting in precipitation of a solid
filtrationThe solid was collected by filtration
washwashed with water
customdried under high vacuum at 100° C.

Sources & evidence

ORD record: ord-65e1ae21d602415396b08b05171de727
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728029B2

Reaction notes

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