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

Reaktionsgleichung

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

Komponenten

Edukt 4

HCID 5234Sodium Chloride

HCID 8028Tetrahydrofuran2×

HCID 2724141Tetrabutylammonium Fluoride

HCID 178443704HCID 178443704, Verbindung

Produkt 1

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

Versuchsvorschrift

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##