Thiophenol → 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:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.COC(C)(C)C>C(Cl)(Cl)Cl>[CH3:1][S:2][C:3](=[CH:8][S:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:4]([O:6][CH3:7])=[O:5]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
3.50 g (11.6 mmol) of methyl 2-(methylthio)-3-(p-toluenesulfonyloxy)-2-propenoate was dissolved in 20 ml of chloroform and cooled to 0° C. To the solution was added 1.28 g (11.6 mmol) of thiophenol and 2 ml (14.3 mmol) of triethylamine and stirred at room temperature for 1 hour. To the reaction mixture was added tert-butyl methyl ether and washed sequentially with an aqueous 1N NaOH solution and a saturated NaCl solution. The organic layer was dried and then concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain 1.64 g of methyl 2-(methylthio)-3-(phenylthio)-2-propenoate.
Workup
- washwashed sequentially with an aqueous 1N NaOH solution
- customThe organic layer was dried
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)
Sources & evidence
- ORD record
- ord-089349c3a4d4489597c99abbbeffcfba
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278473B2
Reaction notes
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