2-Methyl-2-butene → 4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2'-methylbiphenyl-2-carboxylic acid

HRID 1950890Notes

Reaction equation

HRID 1950890 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].CC(=CC)C.[F:16][C:17]1[CH:18]=[CH:19][C:20]([O:43][CH3:44])=[C:21]([C:23]2[N:27]=[C:26]([C:28]3[CH:29]=[C:30]([CH:41]=[O:42])[C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[CH3:40])=[CH:32][CH:33]=3)[O:25][N:24]=2)[CH:22]=1>O.O1CCOCC1>[F:16][C:17]1[CH:18]=[CH:19][C:20]([O:43][CH3:44])=[C:21]([C:23]2[N:27]=[C:26]([C:28]3[CH:29]=[C:30]([C:41]([OH:6])=[O:42])[C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[CH3:40])=[CH:32][CH:33]=3)[O:25][N:24]=2)[CH:22]=1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866823724-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2'-methylbiphenyl-2-carbaldehyde

Product 1

HCID 252554834-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2'-methylbiphenyl-2-carboxylic acidYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium chlorite (59 mg; 0.65 mmol; 5.5 eq.) and sodium dihydrogenphosphate (51 mg; 0.43 mmol; 3.6 eq.) in water (1 mL) was added to a mixture of 2-methyl-2-butene (0.13 mL) and 4-[3-(5-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2′-methylbiphenyl-2-carbaldehyde (46.2 mg; 0.12 mmol; 1 eq.) in dioxane (1 mL) and the reaction was stirred at room temperature for 16 hours. The suspension was partitioned between water and ethyl acetate. The aqueous phase was acidified to pH 3-4 with acetic acid and extracted with ethyl acetate. The combined organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (43 mg; 89%) as a white solid.

Workup

  1. customThe suspension was partitioned between water and ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5956a4e1a4134c92a02f0d77f6a9e197
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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