2-Methyl-2-butene → HCID 71117907, compound

HRID 2368488Notes

Reaction equation

HRID 2368488 reaction equation
Cl([O-])=O.[Na+].[OH:5]P([O-])(O)=O.[Na+].[F:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]([CH:23]=[O:24])=[CH:21][N:20]=[C:19]2[C:25]2[C:30]([F:31])=[CH:29][CH:28]=[C:27]([F:32])[C:26]=2[F:33])=[CH:14][CH:13]=1.CC(=CC)C>O.C(O)(C)(C)C.C(OCC)(=O)C>[F:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[C:22]([C:23]([OH:5])=[O:24])=[CH:21][N:20]=[C:19]2[C:25]2[C:30]([F:31])=[CH:29][CH:28]=[C:27]([F:32])[C:26]=2[F:33])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86677548HCID 86677548, compound

Product 1

HCID 71117907HCID 71117907, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium chlorite (80%, 2.53 g, 22.5 mmol), sodium phosphate mono-basic (210.6 mg, 1.76 mmol) in water was added to a solution of 1-(4-fluorophenyl)-2-(2,3,6-trifluorophenyl)-1H-imidazole-5-carb aldehyde (26) (720 mg, 2.25 mmol) and 2-methyl-2-butene (2M in THF, 7.53 mL, 15.1 mmol) in tert-butanol and the reaction was stirred for 15 minutes. Water and ethyl acetate were added and the layers were separated. The organic layer was washed with saturated sodium bicarbonate. The aqueous layer was acidified to pH 6 with 2N HCl and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give 1-(4-fluorophenyl)-2-(2,3,6-trifluorophenyl)-1H-imidazole-5-carboxylic acid (27).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2364b6d2b4d40faa77e759559d52983
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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