Sodium periodate → HCID 86667504, compound

HRID 533159Notes

Reaction equation

HRID 533159 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][O:8][C:9]([C:11]1[C:16]([CH2:17][CH:18]=C)=[CH:15][C:14]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:13][N:12]=1)=[O:10]>O.C1COCC1.[Os](=O)(=O)(=O)=O>[CH3:7][O:8][C:9]([C:11]1[C:16]([CH2:17][CH:18]=[O:2])=[CH:15][C:14]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:13][N:12]=1)=[O:10]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 68008351HCID 68008351, compound

Product 1

HCID 86667504HCID 86667504, compoundYield 123%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium metaperiodate (304 mg, 1.42 mmol) was added to a stirred solution of 3-allyl-5-phenoxymethyl-pyridine-2-carboxylic acid methyl ester (161 mg, 0.57 mmol) and osmium tetraoxide (0.37 mL, 0.028 mmol; 2.5% in tert-butanol) in H2O (3 mL) and THF (6 mL) at 0° C. The mixture was stirred at RT for 2 h. The mixture was diluted with H2O and extracted with EtOAc. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 3-(2-oxo-ethyl)-5-phenoxymethyl-pyridine-2-carboxylic acid methyl ester (200 mg, 60% purity, 74%) as a black residue which was used in the next step without further purification.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-bad2add163464e76a1bedd6b89dade27
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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