Sodium periodate → Methyl 3-(4-(3-acetyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

HRID 534858Notes

Reaction equation

HRID 534858 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([C:14]2[N:15]=[C:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[O:17][CH:18]=2)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)C.I([O-])(=O)(=O)=[O:26].[Na+]>CC(C)=O.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[C:2]([C:4]1[CH:5]=[C:6]([C:14]2[N:15]=[C:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[O:17][CH:18]=2)[CH:7]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:9]=1)(=[O:26])[CH3:1]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 66750872Methyl 3-(4-(3-(prop-1-en-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

Product 1

HCID 66750826Methyl 3-(4-(3-acetyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoateYield 73%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl 3-(4-(3-(prop-1-en-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 49, 0.175 g, 0.516 mmol), and osmium tetroxide solution (0.21 g, 4 wt % in water, 0.033 mmol) in acetone (10.0 mL) and water (3.0 mL) was added sodium periodate (0.331 g, 1.55 mmol) at room temperature and the mixture was stirred at room temperature for 2 h. After this time, the reaction mixture was diluted with ethyl acetate, washed with water and saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate 9:1) to provide methyl 3-(4-(3-acetyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (0.128 g, 73%) as a white solid: ESI MS m/z 342 [M+H]+.

Workup

  1. washwashed with water and saturated sodium chloride
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-be1e01c64895424b8e2b96bcb91423f2
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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