2-Methyl-2-butene → 5-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acid

Reaction equation

[CH2:1]([C:3]1[NH:7][C:6]([CH:8]=[O:9])=[N:5][C:4]=1[C:10]([F:13])([F:12])[F:11])[CH3:2].Cl([O-])=[O:15].[Na+].P([O-])(O)(O)=O.[Na+].CC(=CC)C>>[CH2:1]([C:3]1[NH:7][C:6]([C:8]([OH:15])=[O:9])=[N:5][C:4]=1[C:10]([F:12])([F:13])[F:11])[CH3:2]

Participants

Reactant 4

HCID 105532-Methyl-2-butene

HCID 23668197Sodium Chlorite

HCID 23672064Monosodium phosphate

HCID 866484875-Ethyl-4-(trifluoromethyl)-1H-imidazole-2-carbaldehyde

Product 1

HCID 675485585-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carboxylic acidYield 99%

Procedure

The same operation as in Example (33c) was performed using 5-ethyl-4-(trifluoromethyl)-1H-imidazole-2-carbaldehyde obtained in Example (39d) (110 mg, 0.57 mmol), sodium chlorite (108 mg, 1.19 mmol), sodium dihydrogenphosphate (178 mg, 1.14 mmol) and 2-methyl-2-butene (0.3 mL, 2.84 mmol), to obtain 117.5 mg of the title compound as a white solid (99%).

Sources & evidence

ORD record: ord-f265397437e240ccbb8b68734156dcdb
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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