Potassium Hydroxide → 4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic Acid

HRID 1961291Notes

Reaction equation

[CH2:1]([N:3]1[C:7]([C:8]2[CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[S:11][CH:12]=2)=[C:6]([CH3:17])[CH:5]=[N:4]1)[CH3:2].[OH-].[K+]>C1COCC1.O>[CH2:1]([N:3]1[C:7]([C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[S:11][CH:12]=2)=[C:6]([CH3:17])[CH:5]=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (270 mg, 1.08 mmol) in THF/H2O (2 mL/0.4 mL) was added KOH (303 mg, 1.79 mmol). The reaction mixture was heated to 50° C. for 4 h. After the mixture was concentrated and diluted with H2O, the pH was adjusted to 3. The mixture was extracted with DCM (5 mL×3). The collected organic layers were concentrated under vacuum to give the crude acid (240 mg), which was used directly in the next step without further purification: LC-MS m/z=237 (M+H)+.

Workup

concentrationAfter the mixture was concentrated
additiondiluted with H2O
extractionThe mixture was extracted with DCM (5 mL×3)
concentrationThe collected organic layers were concentrated under vacuum

Sources & evidence

ORD record: ord-16373eed749a4c699ed29b5c799035e6
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410158B2

Reaction notes

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