Acetone → HCID 118468300, compound

HRID 629464Notes

Reaction equation

HRID 629464 reaction equation
[CH3:1][C:2]1[C:3]([CH:21]=C)=[C:4]([CH:9]=[C:10]([CH2:13][C:14]2[CH:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].CC(C)=[O:25].C(#N)C.I([O-])(=O)(=O)=O.[Na+]>[Os]=O.O>[CH:21]([C:3]1[C:2]([CH3:1])=[C:11]([CH3:12])[C:10]([CH2:13][C:14]2[CH:15]=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])=[O:25]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 118468112HCID 118468112, compound

Product 1

HCID 118468300HCID 118468300, compound

Reagents, catalysts & solvents 2

HCID 142273OxoosmiumCatalyst2×HCID 962WaterSolvent

Procedure

To a solution of methyl 3,4-dimethyl-5-((6-methylpyridin-3-yl)methyl)-2-vinylbenzoate (0.49 g) in a mixed solvent of acetone (6.10 mL)-acetonitrile (6.10 mL)-water (6.10 mL) were added osmium oxide (fixed catalyst I) (0.21 g) and sodium periodate (1.79 g), and the mixture was stirred overnight at room temperature. The reaction mixture was filtered, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (0.47 g) as a crude product. This compound was used in the next step without an additional purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8bcd8f9fca864c62a7bf5516de9d62a8
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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