Dimethyl Sulfoxide → 3-Chloro-5-(2-propen-1-yloxy)pyridine

HRID 1266972Notes

Reaction equation

HRID 1266972 reaction equation
[Na].[CH2:2]([OH:5])[CH:3]=[CH2:4].[Cl:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11](Cl)[CH:12]=1.CS(C)=O>O>[CH2:2]([O:5][C:11]1[CH:10]=[N:9][CH:8]=[C:7]([Cl:6])[CH:12]=1)[CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7858Allyl AlcoholHCID 171533,5-DichloropyridineHCID 5360545Sodium

Product 1

HCID 224785393-Chloro-5-(2-propen-1-yloxy)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Sodium (4.7 g, 203 mmol) was added to allyl alcohol (57.5 ml, 84.5 mmol). After complete reaction, the excess of allyl alcohol was evaporated. 3,5-Dichloropyridine (25.0 g, 169 mmol) and dimethyl sulfoxide (75 ml) were added to the crude mixture. The mixture was stirred at 60° C. overnight. Water (100 ml) was added followed by extraction twice with ethyl acetate (100 ml). The product was isolated in quantitative yield.

Workup

  1. customAfter complete reaction
  2. customthe excess of allyl alcohol was evaporated
  3. extractionfollowed by extraction twice with ethyl acetate (100 ml)
  4. customThe product was isolated in quantitative yield

Sources & evidence

ORD record
ord-068a9cc857f249c4b49656f1f9a9e46a
Source dataset
uspto-grants-2003_04
Patent number
US06552012B2

Reaction notes

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