Glycol monopropyl ether → HCID 18461246, compound

HRID 840657Notes

Reaction equation

HRID 840657 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 18461246HCID 18461246, compoundYield 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-80151212ae704536ac7ba3170f3e6cca
Source dataset
uspto-grants-2002_04
Patent number
US06369083B1

Reaction notes

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