Sodium Chloride → 2-Fluoro-6-(4-hydroxyphenyl)-3-octyloxypyridine

HRID 1780565Notes

Reaction equation

HRID 1780565 reaction equation
C([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([F:17])[C:14]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:13][CH:12]=2)=[C:7](O[SiH](C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].[O:61]1CCCC1>>[F:17][C:15]1[C:14]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:13][CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([OH:61])=[CH:6][CH:7]=2)[N:16]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 178443704HCID 178443704, compound

Product 1

HCID 1357947772-Fluoro-6-(4-hydroxyphenyl)-3-octyloxypyridine

Procedure

4.30 g (8.00 mmol) of 6-(4-tert.-butyldiphenylsilyloxyphenyl)-2-fluoro-3-octyloxypyridine are stirred in 16 ml of a 1-molar tetrabutylammonium fluoride solution in tetrahydrofuran and 50 ml of tetrahydrofuran at room temperature for 2 hours. Sodium chloride solution is then added, the resulting mixture is extracted with ether, the ether phase is washed with sodium chloride solution, dried over sodium sulfate, evaporated to dryness, and the residue is purified by chromatography (silica gel, 8:2 hexane/ethyl acetate), giving 2.16 g of 2-fluoro-6-(4-hydroxyphenyl)-3-octyloxypyridine. ##STR47##

Workup

  1. extractionthe resulting mixture is extracted with ether
  2. washthe ether phase is washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customthe residue is purified by chromatography (silica gel, 8:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c87fede7f3bc419f961dc60bda01bf3c
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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