Methyl alpha-methylthio-alpha-(m-(alpha,alpha-dimethoxybenzyl)phenyl)propionate → Methyl alpha-[m-(alpha,alpha-dimethoxybenzyl)phenyl]propionate
Reaction equation
CS[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([O:24][CH3:25])([O:22][CH3:23])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5]>C(O)C.[Ni]>[CH3:23][O:22][C:15]([C:11]1[CH:10]=[C:9]([CH:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])[CH:14]=[CH:13][CH:12]=1)([O:24][CH3:25])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Participants
4
Procedure
Methyl α-methylthio-α-[m-(α,α-dimethoxybenzyl)phenyl]-propionate (211 mg) was dissolved in 1 ml of ethanol, and 5 ml of an ethanol suspension of 2 cc of Raney nickel (W-II) was added. The mixture was stirred at room temperature for 1 hour. The insoluble matter was separated by filtration, and washed with 40 ml of ethanol. The filtrate and the washing were combined and concentrated under reduced pressure, and 30 ml of methylene chloride was added to the residue. The insoluble matter was separated by filtration, and the solvent was evaporated off under reduced pressure to afford 159 mg of methyl α-[m-(α,α-dimethoxybenzyl)phenyl]propionate as an oil in a yield of 86%.
Workup
- additionwas added
- customThe insoluble matter was separated by filtration
- washwashed with 40 ml of ethanol
- concentrationconcentrated under reduced pressure, and 30 ml of methylene chloride
- additionwas added to the residue
- customThe insoluble matter was separated by filtration
- customthe solvent was evaporated off under reduced pressure
Sources & evidence
- ORD record
- ord-6186a229d2314f96b391e1f6e7ac94d2
- Source dataset
- uspto-grants-1981_12
- Patent number
- US04308208
Reaction notes
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