methyl 2-methyl-3-sulfanylpropanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of methyl 2-methyl-3-mercaptoproponate (1.34 g, 10 mmol) and methanol (0.42 g, 10 mmole) is added to a mixture of bis(2,2,2-trifluoroethoxy)triphenylphosphorane (11 mmole) [prepared in situ from triphenylphosphine (12 mmole) and sodium 2,2,2-trifluoro ethoxide (24 mmole) in dry diethyl ether (20 ml)] in dichloromethane (20 ml). After 20 hours stirring at room temperature the mixture is poured into water and extracted with ether. The ether extract is washed with 5% aqueous sodium hydroxide and dried over magnesium sulfate. The solution is evaporated, solids removed by filtration and the oily residue purified by vacuum distillation yielding methyl-3-methylthio-2-methylpropanoate. extracted with ether The ether extract is washed with 5% aqueous sodium hydroxide dried over magnesium sulfate The solution is evaporated solids removed by filtration the oily residue purified by vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of methyl 2-methyl-3-mercaptoproponate (1.34 g, 10 mmol) and methanol (0.42 g, 10 mmole) is added to a mixture of bis(2,2,2-trifluoroethoxy)triphenylphosphorane (11 mmole) [prepared in situ from triphenylphosphine (12 mmole) and sodium 2,2,2-trifluoroethoxide (24 mmole) in dry diethyl ether (20 ml)] in dichloromethane (20 ml). After 20 hours stirring at room temperature the mixture is poured into water and extracted with ether. The ether extract is washed with 5% aqueous sodium hydroxide and dried over magnesium sulfate. The solution is evaporated, solids removed byy filtration and the oily residue purified by vacuum distillation yielding methyl-3-methylthio-2-methylpropanoate. extracted with ether The ether extract is washed with 5% aqueous sodium hydroxide dried over magnesium sulfate The solution is evaporated solids removed byy filtration the oily residue purified by vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using the procedure described in Example I 33 grams (0.25 m) of methyl 3-mercapto-2-methylpropionate and 10 grams (0.25 m) of NaOH was caused to react with acetohydroximoyl chloride prepared from 15 g (0.25 m) of acetaldoxime and 18 g (0.25 m) of chlorine. After reaction the crude reaction product was placed in a pyrex pressure bottle to which was added 200 ml of concentrated ammonium hydroxide. The bottle was sealed and the mixture was stirred by means of a magnetic stirring bar for two days at ambient temperature. The bisphasic reaction mixture was then extracted with ether and the lower, aqueous phase was concentrated in vacuo to produce 3 g of a residue which crystallized on standing. An infrared spectrum supported the proposed structure. After reaction the crude reaction product The bottle was sealed The bisphasic reaction mixture was then extracted with ether the lower, aqueous phase was concentrated in vacuo