반응 #160419

반응 방정식

2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid ethyl ester

lithium hydroxide monohydrate

→

2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid

수율 105.9%

용매

THF water

NaHCO3 brine

반응 조건

후처리

1. 1
   농축The reaction was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in water (10 mL)
3. 3
   세척washed with diethyl ether (2×25 mL)
4. 4
   온도The aqueous layer was cooled in an ice bath
5. 5
   추출The acidic aqueous layer was extracted with ethyl acetate (2×50 mL) and with isopropanol/chloroform (3×50 mL)
6. 6
   건조The combined organic extracts were dried over Na2SO4
7. 7
   여과filtered

실험 절차

To a solution of 769 mg (2.77 mmol) of 2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid ethyl ester in THF/water (1/1, 10 mL) were added 228 mg (5.43 mmol) of lithium hydroxide monohydrate. The reaction was stirred at room temperature for 18 h. The reaction was concentrated under reduced pressure. The residue was dissolved in water (10 mL) and washed with diethyl ether (2×25 mL). The aqueous layer was cooled in an ice bath and then acidified with 1M aqueous HCl solution to pH 2. The acidic aqueous layer was extracted with ethyl acetate (2×50 mL) and with isopropanol/chloroform (3×50 mL). The combined organic extracts were dried over Na2SO4 and filtered. Concentration of the filtrate under reduced pressure afforded 734 mg of 2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid.

출처