反应详情

A solution of 0.86 g (15.2 mmol) of potassium hydroxide in ethanol (78 mL, degassed and under nitrogen) was added to 0.81 g (4.66 mmol) of thioacetic acid S-(tetrahydro-pyran-4-ylmethyl)ester. The reaction was stirred at room temperature under nitrogen for 0.5 h. Then 2.1 mL (14.1 mmol) of ethyl α-bromoisobutyrate were added and the reaction stirred for 4 h. The resulting precipitate was removed by filtration and the filtrate concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and washed with saturated aqueous NaHCO3 (50 mL), brine (50 mL) and dried over Na2SO4. Filtration and concentration of the filtrate under reduced pressure, followed by column chromatography of the residue (silica, eluent: heptanes, 0-20% ethyl acetate) afforded 0.76 g of 2-methyl-2-(tetrahydro-pyran-4-ylmethylsulfanyl)-propionic acid ethyl ester.

1. stirringthe reaction stirred for 4 h
2. customThe resulting precipitate was removed by filtration
3. concentrationthe filtrate concentrated under reduced pressure
4. dissolutionThe residue was dissolved in DCM (100 mL)
5. washwashed with saturated aqueous NaHCO3 (50 mL), brine (50 mL)
6. dry with materialdried over Na2SO4
7. filtrationFiltration and concentration of the filtrate under reduced pressure