Benzyl Chloride → HCID 20212031, compound

HRID 1906472Notes

Reaction equation

HRID 1906472 reaction equation
[I:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.[O-]CC.[Na+].[Na].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.CS(C)=O.C(O)C>[I:1][C:2]1[C:7]([O:8][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 7503Benzyl ChlorideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 20212017HCID 20212017, compound

Product 1

HCID 20212031HCID 20212031, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

2-Iodo-3-hydroxy-5-methylpyridine (13.5 g, 57.4 m.mole) was added to a solution of sodium ethoxide (57.4 m.mole, prepared freshly from sodium and dry ethanol (100 ml)). Dry dimethyl sulfoxide (250 ml) was added, and the ethanol was removed by distillation under reduced pressure. Benzyl chloride (7.27 g, 57.4 mole) was added portionwise with cooling and then the mixture was heated at 90°14 100° for 15 hours. The dimethyl sulfoxide was boiled off under reduced pressure, water was added (100 ml) and the product was extracted from this with chloroform. After drying with magnesium sulfate and evaporation under reduced pressure, a crude product was obtained (17.62 g, 94% yield) a tiny portion of which, after heating in water and then recrystallising from methanol-water, gave 2-iodo-3-benzyloxy-5-methylpyridine which was pure by N.M.R. (mp 83°-5°).

Workup

  1. customthe ethanol was removed by distillation under reduced pressure
  2. temperaturewith cooling
  3. temperaturethe mixture was heated at 90°14 100° for 15 hours
  4. additionwas added (100 ml)
  5. extractionthe product was extracted from this with chloroform
  6. dry with materialAfter drying with magnesium sulfate and evaporation under reduced pressure
  7. customa crude product was obtained (17.62 g, 94% yield) a tiny portion of which
  8. customrecrystallising from methanol-water

Sources & evidence

ORD record
ord-aabdfe6b147947709c56b9a850c24716
Source dataset
uspto-grants-1987_03
Patent number
US04652572

Reaction notes

Loading…