[O:1]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[CH:14]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][S:17]([CH2:19][S:20][CH3:21])=[O:18]>C1COCC1.CO.ClCCl>[CH3:16][S:17]([C:19]([S:20][CH3:21])=[CH:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:18]To a stirred solution of 4-phenoxy-3-pyridinecarboxaldehyde (0.687 g, 3.45 mmol) and methyl methylsulphinylmethyl sulphide (0.429 g, 3.45 mmol) in THF was added dropwise Triton B (0.53 ml, 40% solution in methanol). The mixture was heated at reflux for 2 hours, allowed to cool and then diluted with dichloromethane (150 ml). The solution was washed with saturated brine (2×) and the solvent was evaporated. Flash chromatography (eluent ether-ethyl acetate) of the resulting residue gave 3-(2'-methylsulphinyl-2'-methylthiovinyl)-4-phenoxypyridine as a pale yellow gum (0.128 g); 1H NMR delta (CDCl3) 2.32 (3H,s), 2.77 (3H,s), 6.60 (1H,d), 6.9-7.5 (5H,m), 7.93 (1H,s), 8.32 (1H,d), 9.10 (1H,s).
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