Water → 2-Chloro-4-ethoxypyridine

HRID 336365Notes

Reaction equation

HRID 336365 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Cl:5][C:6]1[CH:11]=[C:10](I)[CH:9]=[CH:8][N:7]=1.O>C(O)C>[Cl:5][C:6]1[CH:11]=[C:10]([O:1][CH2:2][CH3:3])[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 15165112-Chloro-4-iodopyridineHCID 2723922Sodium ethoxide

Product 1

HCID 8172382-Chloro-4-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

33 ml sodium ethoxide was added to 19.2 g 2-chloro-4-iodopyridine in 150 mL ethanol. The reaction was refluxed overnight. Then water was added and extracted with tert-butyl-methylether. The organic layer was evaporated and the residue cleanded by chromatography on silica gel (petrolether/EtOAC:9/1) to yield 5 g of the desired compound.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. extractionextracted with tert-butyl-methylether
  3. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-7e9bb253fda943609dc5924bd9ff0b20
Source dataset
uspto-grants-2014_11
Patent number
US08889677B2

Reaction notes

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