S(Cl)([Cl:3])=O.N1C=CC=CC=1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][Cl:3])=[CH:20][CH:19]=1
A stirred solution of 4.4 gram (0.037 mole) of thionyl chloride in 75 mL of dry methylene chloride was cooled to 0° C., and 0.07 gram (catalyst) of pyridine was added. A solution of 5.0 grams (0.025 mole) of (4-(2-pyridyloxy)phenyl)methanol in 25 mL of methylene chloride was then added drop wise. Upon completion addition of addition, the reaction mixture was allowed to warm to 22° C. where it stirred for 30 minutes. After this time an aliquot of the reaction mixture was taken up in ethyl acetate and treated with solid sodium bicarbonate. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure to a residue. The NMR spectrum was consistent with the proposed structure. Inasmuch as this compound is unstable, it was used without further purification. The yield was estimated at about 5.0 grams.
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