Thiophenol → HCID 12505694, compound
Reaction equation
[CH3:1]/[C:2](=[CH:7]\OS(C1C=CC(C)=CC=1)(=O)=O)/[C:3]([O:5][CH3:6])=[O:4].[C:19]1([SH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.COC(C)(C)C>C(Cl)(Cl)Cl>[CH3:7]/[C:2](=[CH:1]\[S:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)/[C:3]([O:5][CH3:6])=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
11.0 g (40.7 mmol) of (E)-methyl 2-methyl-3-(p-toluenesulfonyloxy)-2-propenoate was dissolved in 100 ml of chloroform and 6.3 g (57.0 mmol) of thiophenol and 33 ml of triethylamine were added. The solution was stirred at 50° C. for 9 hours. To the reaction mixture was added tert-butyl methyl ether and washed sequentially with an aqueous 1N NaOH solution and a saturated NaCl solution, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain 6.5 g of (E)-methyl 2-methyl-3-(phenylthio)-2-propenoate.
Workup
- washwashed sequentially with an aqueous 1N NaOH solution
- dry with materiala saturated NaCl solution, dried
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)
Sources & evidence
- ORD record
- ord-9af2fe94b3f54d4c92b3ff5ae1348ae7
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278473B2
Reaction notes
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