Water → HCID 118468296, compound

HRID 629474Notes

Reaction equation

HRID 629474 reaction equation
[CH2:1]([C:3]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[CH:16][CH:15]=2)=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH:26]=C)[CH:4]=1)[CH3:2].I([O-])(=O)(=O)=[O:29].[Na+].C(#N)C.O>[Os]=O.CC(C)=O>[CH2:1]([C:3]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:24]=[CH:23][N:22]([CH3:25])[N:21]=3)=[CH:16][CH:15]=2)=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH:26]=[O:29])[CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 118468311HCID 118468311, compound

Product 1

HCID 118468296HCID 118468296, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 142273OxoosmiumCatalyst2×HCID 180AcetoneSolvent

Procedure

A mixture of methyl 4-ethyl-5-(4-(1-methyl-1H-pyrazol-3-yl)benzyl)-2-vinylbenzoate (0.21 g), osmium oxide (fixed catalyst I) (0.08 g) and sodium periodate (0.64 g) in acetone (4.00 mL)-acetonitrile (4.00 mL)-water (4.00 mL) was stirred overnight at room temperature. The insoluble substance was removed by filtration, the filtrate was diluted with ethyl acetate, and the mixture was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (0.21 g) as a crude product. This compound was used in the next step without an additional purification.

Workup

  1. customThe insoluble substance was removed by filtration
  2. additionthe filtrate was diluted with ethyl acetate
  3. washthe mixture was washed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7af20e0a4e4e40dbaaddf91dd585fac2
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

Loading…