methyl 2-(3,3,3-trifluoropropylsulfanyl)acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 10 g of methyl thioglycolate and 21 g of 1-iodo-3,3,3-trifluoropropane in 200 ml of N,N-dimethylformamide, 13 g of potassium carbonate was added under ice-cooling, and then stirred at room temperature for 20 hours. To the reaction mixture, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was washed sequentially with 10% hydrochloric acid and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product comprising methyl (3,3,3-trifluoropropylthio)acetate. The obtained crude product was dissolved in 100 ml of glacial acetic acid, and 50 ml of peracetic acid (32% (w/w) acetic acid solution) was added thereto under ice-cooling. The mixture was stirred at 60° C. for 16 hours. In the middle of the reaction, the formation of a compound that was presumed to be in a sulfoxide form was confirmed by TLC (thin layer chromathgraphy) analysis. The reaction mixture was allowed to stand to cool to nearly room temperature, poured into water and then extracted with ethyl acetate. The organic layer was washed sequentially with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 14.1 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate. cooling followed by extraction with ethyl acetate The organic layer was washed sequentially with 10% hydrochloric acid a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate concentrated under reduced pressure to obtain a crude product The obtained crude product under ice-cooling The mixture was stirred at 60° C. for 16 hours In the middle of the reaction to cool to nearly room temperature extracted with ethyl acetate The organic layer was washed sequentially with a saturated sodium hydrogen carbonate aqueous solution a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 10 g of methyl thioglycolate and 21 g of 1-iodo-3,3,3-trifluoropropane in 200 ml of N,N-dimethylformamide, 13 g of potassium carbonate was added under ice-cooling, and then stirred at room temperature for 20 hours. To the reaction mixture, 10% hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was washed sequentially with 10% hydrochloric acid and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product comprising methyl (3,3,3-trifluoropropylthio)acetate. The obtained crude product was dissolved in 100 ml of glacial acetic acid, and 50 ml of peracetic acid (32% (w/w) acetic acid solution) was added thereto under ice-cooling. The mixture was stirred at 60° C. for 16 hours. In the middle of the reaction, the formation of a compound that was presumed to be in a sulfoxide form was confirmed by TLC (thin layer chromathgraphy) analysis. The reaction mixture was allowed to stand to cool to nearly room temperature, poured into water and then extracted with ethyl acetate. The organic layer was washed sequentially with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 14.1 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate. cooling followed by extraction with ethyl acetate The organic layer was washed sequentially with 10% hydrochloric acid a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate concentrated under reduced pressure to obtain a crude product The obtained crude product under ice-cooling The mixture was stirred at 60° C. for 16 hours In the middle of the reaction to cool to nearly room temperature extracted with ethyl acetate The organic layer was washed sequentially with a saturated sodium hydrogen carbonate aqueous solution a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate concentrated under reduced pressure