Dichloromethane → (E)-2-ethyl-5-(2-methylsulphanyl-2-methylsulphinyl-vinyl)-1,3-dimethoxybenzene
Reaction equation
[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[CH2:13]([C:15]1[C:22]([O:23][CH3:24])=[CH:21][C:18]([CH:19]=O)=[CH:17][C:16]=1[O:25][CH3:26])[CH3:14].[CH3:27][S:28][CH2:29][S:30]([CH3:32])=[O:31].C(Cl)Cl>CO.O1CCCC1>[CH2:13]([C:15]1[C:22]([O:23][CH3:24])=[CH:21][C:18](/[CH:19]=[C:29](\[S:28][CH3:27])/[S:30]([CH3:32])=[O:31])=[CH:17][C:16]=1[O:25][CH3:26])[CH3:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
130 ml of a 40% solution of benzyltrimethylammonium hydroxide in methanol (Triton B) were added to a solution of 126.5 g (651.2 mmol) of 4-ethyl-3,5-dimethoxy-benzaldehyde and 80.89 g (651.2 mmol) of methyl methylthiomethyl sulphoxide in 300 ml of tetrahydrofuran and the mixture was heated at reflux for 5 hours. After the addition of 300 ml of methylene chloride the mixture was extracted with 200 ml of 0.5M sulphuric acid. The organic phase was dried (MgSO4), filtered and evaporated. Chromatography of the resulting residue (silica gel, ethyl acetate/hexane 1:1) yielded 134.6 g (69%) of (E)-2-ethyl-5-(2-methylsulphanyl-2-methylsulphinyl-vinyl)-1,3-dimethoxybenzene as a colorless oil, which gave colorless crystals of m.p. 82-83° by crystallization from hexane.
Workup
- temperaturethe mixture was heated
- temperatureat reflux for 5 hours
- extractionwas extracted with 200 ml of 0.5M sulphuric acid
- dry with materialThe organic phase was dried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-6b296ae9770746edb8c95f4eb3ae2249
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310208B1
Reaction notes
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