Sulfuric Acid → Methyl 2-(3,4-dichlorophenyl)-2-(3-oxobutylthio)acetate
Reaction equation
C([CH:4]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=1)[C:5]([O:7][CH3:8])=[O:6])(=S)C.[S:17](=O)(=O)(O)O.[CH:22]([C:24]([CH3:26])=[O:25])=[CH2:23].C(N(CC)CC)C>C(OCC)(=O)C.CO>[Cl:16][C:11]1[CH:10]=[C:9]([CH:4]([S:17][CH2:23][CH2:22][C:24](=[O:25])[CH3:26])[C:5]([O:7][CH3:8])=[O:6])[CH:14]=[CH:13][C:12]=1[Cl:15]Participants
Conditions
- Temperature
- 60 °C
Procedure
To a methanol (2 mL) solution of methyl 2-thioacetyl-2-(3,4-dichlorophenyl)acetate (0.50 g, 1.7 mmol), concentrated sulfuric acid (0.050 mL, 0.55 equivalent amount) was added, followed by stirring at 60° C. for 3 hours. After the reaction solution was cooled to room temperature, it was dropwise added to an ethyl acetate (2 mL) solution of methyl vinyl ketone (0.17 mL, 1.2 equivalent amounts) and triethylamine (0.36 mL, 1.5 equivalent amount) at room temperature. The reaction solution was mixed with ethyl acetate (1 mL), followed by liquid separation with a mixed liquid of water-saturated salt solution (1:1, (v/v)), and further, the organic layer was washed with a saturated ammonium chloride aqueous solution and a saturated salt solution and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to give the desired product as a colorless oil (0.42 g, yield: 76%).
Workup
- temperatureAfter the reaction solution was cooled to room temperature
- customfollowed by liquid separation with a mixed liquid of water-saturated salt solution (1:1, (v/v))
- washfurther, the organic layer was washed with a saturated ammonium chloride aqueous solution
- dry with materiala saturated salt solution and dried over anhydrous magnesium sulfate
- customThe drying agent was removed by filtration
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-3dfcbd01f2134e3685e314a14f312a29
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399685B2
Reaction notes
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