[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(C=P(CCCC)(CCCC)CCCC)#N.[F:24][C@@H:25]([CH3:28])[CH2:26]O.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:24][C@@H:25]([CH3:28])[CH2:26][O:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1A solution of 1.5 g of 4-hydroxypyridine, 7.6 g of cyanomethylenetributylphosphorane, and 1.4 g of (2S)-2-fluoro-1-propanol in 20 mL of toluene was stirred at 105° C. overnight. To the reaction mixture were added 1 M hydrochloric acid and ethyl acetate, and the organic layer was separated. The aqueous layer was adjusted to pH 11 by the addition of a 1 M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 2.2 g of 4-{[(2S)-2-fluoropropyl]oxy}pyridine.
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