Sodium periodate → HCID 90389328, compound

HRID 1526628Notes

Reaction equation

HRID 1526628 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][F:11])[C:5]([CH:8]=C)=[N:6][CH:7]=1.I([O-])(=O)(=O)=[O:13].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][F:11])[C:5]([CH:8]=[O:13])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 90389316HCID 90389316, compound

Product 1

HCID 90389328HCID 90389328, compoundYield 83.4%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-3-(fluoromethyl)-2-vinylpyridine (65 mg, 0.38 mmol) in THF (2.3 mL) and water (3.5 mL) was added a solution of osmium tetroxide (2.5 wt % in 2-methyl-2-propanol, 80 μl, 0.038 mmol, Aldrich). After 5 min, sodium meta-periodate (122 mg, 0.568 mmol, Aldrich) was added in one portion and the reaction mixture was allowed to stir for 1 h. The reaction mixture was partitioned between brine and EtOAc. The organic phase was separated and dried over MgSO4. The filtrate was absorbed onto a plug of silica gel and purified by chromatography, eluting with a gradient of 5% to 45% EtOAc in hexane, to provide the title compound as grey solid (55 mg).

Workup

  1. customThe reaction mixture was partitioned between brine and EtOAc
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. customThe filtrate was absorbed onto a plug of silica gel
  5. custompurified by chromatography
  6. washeluting with a gradient of 5% to 45% EtOAc in hexane

Sources & evidence

ORD record
ord-726ef3bcc88a48b1826b70298253097b
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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