1-Octanol → 2-Fluoro-6-octyloxypyridine

HRID 1780551Notes

Reaction equation

HRID 1780551 reaction equation
[CH2:1]([O-:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Li+].C(O)CCCCCCC.C([Li])CCC.[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](F)[N:27]=1.[Cl-].[Na+]>O1CCCC1.CCOCC>[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[N:27]=1

Participants

8

Reactant 5

HCID 9571-OctanolHCID 5234Sodium ChlorideHCID 739342,6-DifluoropyridineHCID 23682185Lithium octanolateHCID 178418339Butyllithium

Product 1

HCID 190469372-Fluoro-6-octyloxypyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium octanolate (previously prepared from 13.02 g (100.00 mmol) of 1-octanol and 69 ml (110.00 mmol) of a 1.6-molar n-butyllithium solution in 40 ml of tetrahydrofuran at 0° C.) and 11.51 g (100.00 mmol) of 2,6-difluoropyridine are refluxed in 40 ml of tetrahydrofuran for 7 hours. The mixture is then distributed between sodium chloride solution and ether, the ether phase is washed twice with sodium chloride, dried over sodium sulfate, filtered and freed from solvent. Purification of the residue by chromatography (silica gel, 9:1 hexane/ethyl acetate) gives 13.48 g (59.80 mmol) of 2-fluoro-6-octyloxypyridine. ##STR21##

Workup

  1. washthe ether phase is washed twice with sodium chloride
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customPurification of the residue by chromatography (silica gel, 9:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d916625809554dffad6092b63ecd21fc
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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