Dimethyl Sulfate → 3,5-Dimethyl-2-hydroxymethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine

HRID 1248975Notes

Reaction equation

HRID 1248975 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][CH2:9][C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12].S(OC)([O:22][CH3:23])(=O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>O.CO>[CH3:1][C:2]1[C:3]([CH2:23][OH:22])=[N:4][CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][CH2:9][C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 62648Ammonium PersulfateHCID 136548073,5-Dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide

Product 1

HCID 149020163,5-Dimethyl-2-hydroxymethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,5-dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide (2.5 g) and dimethyl sulfate (1 ml) was heated at 120° C. for 30 minutes, to which was then added methanol (12.5 ml). To the mixture was added dropwise at 80° C. ammonium persulfate (4.3 g) dissolved in water (20 ml)-methanol (10 ml) over 30 minutes, which was stirred for further 30 minutes. The resultant solution was concentrated. To the residue was added ice, which was neutralized with sodium carbonate, followed by extraction with chloroform. The extract was dried on sodium sulfate, followed by removing the solvent by evaporation to give 2.2 g of 3,5-dimethyl-2-hydroxymethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine as an oily substance.

Workup

  1. concentrationThe resultant solution was concentrated
  2. additionTo the residue was added ice, which
  3. extractionfollowed by extraction with chloroform
  4. customThe extract was dried on sodium sulfate
  5. customby removing the solvent
  6. customby evaporation

Sources & evidence

ORD record
ord-b54aad2f10484b4dada1613305783923
Source dataset
uspto-grants-1986_12
Patent number
US04628098

Reaction notes

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