Sodium Hydroxide → 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid

HRID 268636Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:9]([CH:10]([CH3:12])[CH3:11])=[C:8]([CH:13]=[O:14])[N:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:6]=1)=[O:4].[OH-].[Na+]>CO>[F:21][C:18]1[CH:17]=[CH:16][C:15]([N:7]2[C:8]([CH:13]=[O:14])=[C:9]([CH:10]([CH3:12])[CH3:11])[C:5]([C:3]([OH:4])=[O:2])=[N:6]2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid methyl ester (11.34 g, 39.1 mmol) in MeOH (150 mL) was added NaOH (156 mL of 1 N solution, 156 mmol). The reaction was heated to 60° C. for 4 hr. The solvent was then removed under reduced pressure and water (150 mL) and Et2O (100 mL) were added. The organic layer was discarded and the aqueous layer was acidified with 10% HCl to pH 1 and then extracted with EtOAc (200 mL×2). The combined organic extracts were dried over Na2SO4 and concentrated to give 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid (8.55 g, 79%) as a white solid that required no purification: MS(APCI+): m/z 277.0 (M+H).

Workup

customThe solvent was then removed under reduced pressure and water (150 mL) and Et2O (100 mL)
additionwere added
extractionextracted with EtOAc (200 mL×2)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-86611f2db9cf479ba8834d374198b1d9
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446121B2

Reaction notes

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