Chloroform → Methyl 2-methylthio-3-(phenylthio)acrylate
Reaction equation
[CH3:1][S:2][C:3](=[CH:8]OS(C1C=CC(C)=CC=1)(=O)=O)[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.C(Cl)(Cl)Cl.[C:31]1([SH:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>COC(C)(C)C>[CH3:1][S:2][C:3](=[CH:8][S:37][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:4]([O:6][CH3:7])=[O:5]Participants
6
Procedure
To a mixture of methyl 2-methylthio-3-(p-toluenesulfonyloxy)acrylate (3.05 g), triethylamine (2 mL) and chloroform (20 mL) was added slowly thiophenol (1.28 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added tert-butyl methyl ether, and then a 1N aqueous sodium hydroxide solution, thereby layers were separated. The organic layer was washed with a saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain methyl 2-methylthio-3-(phenylthio)acrylate (1.64 g).
Workup
- temperaturecooling
- customa 1N aqueous sodium hydroxide solution, thereby layers were separated
- washThe organic layer was washed with a saturated aqueous sodium chloride solution
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e6c3e3fde0c7493d84288e854cc5dfc0
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318981B2
Reaction notes
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