Methyl (methylsulfinyl)methyl sulfide → HCID 54404760, compound

Participants

Reaction Steps

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).

Provenance & Evidence