Glycol monopropyl ether → 2-Fluoro-6-(2-propoxyethoxy)pyridine

HRID 2303430Notes

Reaction equation

HRID 2303430 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][OH:7])[CH2:2][CH3:3].CC(C)([O-])C.[K+].F[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[N:16]=1>C1COCC1.[Cl-].[Na+].O>[F:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:7][CH2:6][CH2:5][O:4][CH2:1][CH2:2][CH3:3])[N:16]=1

Participants

6

Reactant 3

HCID 17756Glycol monopropyl etherHCID 739342,6-DifluoropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 184612462-Fluoro-6-(2-propoxyethoxy)pyridineYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

2-Propoxyethanol (1.89 g, 18.1 mmol) was dissolved in 50 mL THF, treated with potassium tert-butoxide (3.05 g, 27.2 mmol), stirred to uniform solution, placed in an addition funnel, and added dropwise to a solution of 2,6-difluoropyridine in 50 mL THF. After stirring overnight at room temperature, the solution was diluted with brine and extracted with ether. The ether extracts were combined and dried over Na2SO4, then concentrated in vacuo to yield 2-fluoro-6-(2-propoxyethoxy)-pyridine (3.33 g, 93%) as a yellow oil.

Workup

  1. customplaced in an addition funnel
  2. stirringAfter stirring overnight at room temperature
  3. extractionextracted with ether
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d152f45c8c1344539e126b851f30d0eb
Source dataset
uspto-grants-2002_08
Patent number
US06432990B1

Reaction notes

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