Methyl (methylsulfinyl)methyl sulfide → 2-Chloro-1-methoxy-3-[2-(methylsulfanyl)-2-(methylsulfinyl)vinyl]benzene
Reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:12][S:13][CH2:14][S:15]([CH3:17])=[O:16]>C1COCC1>[Cl:1][C:2]1[C:3]([CH:4]=[C:14]([S:13][CH3:12])[S:15]([CH3:17])=[O:16])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH3:11]Participants
4
Procedure
To a solution of 2-chloro-3-methoxybenzaldehyde 7a (4.65 g, 27.3 mmol) and methyl (methylthio)methyl sulfoxide (4.3 mL, 43.9 mmol) in THF (25 mL) was added a 40% methanolic solution of Triton B (6.2 mL, 13.6 mmol) and the resulting solution was refluxed for 16 hours. After THF was removed, the residue was taken up in ethyl acetate,washed with 1 N HCl, H2O, and brine, then was dried over Na2SO4, and concentrated. Purification by column chromatography on silica gel with dichloromethane afforded 2-chloro-1-methoxy-3-[2-methylsulfanyl)-2-(methylsulfinyl)vinyl]benzene 7b (3.61 g, 48%) as a yellow oil. GCMS (EI) m/z 225 (M+-Cl16), 210 (M+-Cl-OMe).