Ethyl Bromide → 3-Ethoxy-2-methylpyridine

HRID 128602Notes

Reaction equation

HRID 128602 reaction equation
[Na].[OH:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.Br[CH2:11][CH3:12]>C(O)C>[CH2:11]([O:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 707192-Methylpyridin-3-olHCID 5360545Sodium

Product 1

HCID 128750153-Ethoxy-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium metal (46.2 g) was dissolved in absolute ethanol (1 l) with stirring under nitrogen. 3-Hydroxy-2-methylpyridine (200 g prepared as described in C.A. 48, P4597 h) was added. The mixture was stirred at ambient temperature for 30 minutes and then a solution of bromoethane (350 ml) in absolute ethanol (100 ml) was added. The mixture was boiled under reflux for 5 hours then cooled and filtered. The filtrate was evaporated and the residue partitioned between dichloromethane and water. The organic layer was separated off and the aqueous layer extracted with dichloromethane. The combined organic extracts were dried and evaporated. The residue was distilled to give 3-ethoxy-2-methylpyridine b.p. 80°-84° C. (20 mmHg).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 30 minutes
  2. temperatureunder reflux for 5 hours
  3. temperaturethen cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue partitioned between dichloromethane and water
  7. customThe organic layer was separated off
  8. extractionthe aqueous layer extracted with dichloromethane
  9. customThe combined organic extracts were dried
  10. customevaporated
  11. distillationThe residue was distilled

Sources & evidence

ORD record
ord-c33f66750f284082bf393a82d40ba091
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Reaction notes

Loading…