Sodium Bicarbonate → tert-Butyl 2-chloro-6-formylisonicotinate

HRID 1909134Notes

Reaction equation

HRID 1909134 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH:15]=C)[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].I([O-])(=O)(=O)=[O:18].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH:15]=[O:18])[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 86657031tert-Butyl 2-chloro-6-vinylisonicotinate

Product 1

HCID 86657032tert-Butyl 2-chloro-6-formylisonicotinate

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-chloro-6-vinylisonicotinate (9.6 g, 40.1 mmol) in THF (100 mL) and water (100 mL) were added osmium tetroxide (4% in water; 6.3 mL, 0.80 mmol) and sodium periodate (25.7 g, 120.0 mmol). The mixture was stirred at ambient temperature. After 30 min, saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76d01d924dae4fe0ab5e33d851b881ca
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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