2-Bromopropane → Methyl alpha-methylthio-alpha-(m-phenoxyphenyl)isovalerate
Reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH:23](Br)([CH3:25])[CH3:24].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][S:2][C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)([CH:23]([CH3:25])[CH3:24])[C:4]([O:6][CH3:7])=[O:5]Participants
Procedure
Methyl α-methylthio-(m-phenoxyphenyl)acetate (1.77 g) was dissolved in 10 ml of dimethylformamide, and with ice cooling, 260 mg (65% content) of sodium hydride was added. The mixture was stirred for 30 minutes. Then, 0.70 ml of isopropyl bromide was added, and with ice cooling for 3 minutes, the mixture was stirred at room temperature for 2.5 hours. After adding an aqueous solution of ammonium chloride (1 g/40 ml), the mixture was extracted three times with 50 ml of diethyl ether. The organic layer was washed twice with 20 ml of water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using benzene as an eluent to afford 1.25 g of methyl α-methylthio-α-(m-phenoxyphenyl)isovalerate in a yield of 62%.
Workup
- waitwith ice cooling for 3 minutes
- stirringthe mixture was stirred at room temperature for 2.5 hours
- extractionthe mixture was extracted three times with 50 ml of diethyl ether
- washThe organic layer was washed twice with 20 ml of water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was chromatographed on a silica gel column
Sources & evidence
- ORD record
- ord-dfd3b48d0ef541f8af6e2416d29e87f4
- Source dataset
- uspto-grants-1981_12
- Patent number
- US04308208
Reaction notes
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