Sodium Iodide → 2-(2,6-Dichloropyridin-3-yl)acetaldehyde

HRID 595757Notes

Reaction equation

HRID 595757 reaction equation
[Cl:1][C:2]1[C:7](/[CH:8]=[CH:9]/[O:10]CC)=[CH:6][CH:5]=[C:4]([Cl:13])[N:3]=1.[Na+].[I-].C[Si](Cl)(C)C.C([O-])(O)=O.[Na+]>C(#N)C>[Cl:1][C:2]1[C:7]([CH2:8][CH:9]=[O:10])=[CH:6][CH:5]=[C:4]([Cl:13])[N:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 90332512(E)-2,6-dichloro-3-(2-ethoxyvinyl)pyridine

Product 1

HCID 220381052-(2,6-Dichloropyridin-3-yl)acetaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (E)-2,6-dichloro-3-(2-ethoxyvinyl)pyridine (890 mg, 4.08 mmol) in acetonitrile (10 ml) was added NaI (1.84 g, 12.2 mmol) and TMSCl (887 mg, 8.16 mmol). The resulting mixture was stirred at RT for 4 hours, then treated with NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the yellow oil 2-(2,6-dichloropyridin-3-yl)acetaldehyde (760 mg, yield: 98%). MS (M+H)+: 190.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f0c7cfb2f4243bd94035f0fc5d964e4
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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