Reacción #969846

Ecuación de reacción

4-bromo-1-methoxy-1-oxobutane-2-sulfonic acid

thioacetic acid

DIPEA

→

title compound

Rendimiento 90.0%

4-(Acetylthio)-1-methoxy-1-oxobutane-2-sulfonic acid

Rendimiento 90.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated
2. 2
   workup.DISSOLUTIONThe mixture was redissolved in methanol
3. 3
   Filtraciónfiltered through celite,
4. 4
   Concentraciónconcentrated
5. 5
   Otropurified with SiO2 chromatography
6. 6
   Lavadoeluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1)

Procedimiento

5.0 g (19.2 mmol) of 4-bromo-1-methoxy-1-oxobutane-2-sulfonic acid in 100 ml of THF was added 3.0 ml of thioacetic acid and 9.0 ml of DIPEA in 100 ml of THF. The mixture was stirred overnight then refluxed at 70° C. for 1 hr, evaporated and co-evaporated with 3×100 ml of water after neutralized to pH 7 with NaHCO3. The mixture was redissolved in methanol, filtered through celite, concentrated and purified with SiO2 chromatography eluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1) to afford 4.4 g (90% yield) of the title compound. 1H NMR (D2O) 3.95 (dd, 1H, J=4.1, 10.3 Hz), 3.83 (s, 3H), 3.74 (m, 2H), 3.22 (dd, 2H, J=7.4, 14.9 Hz), 2.39 (s, 3H); 13C NMR 203.88, 172.91, 67.32, 56.17, 29.04, 20.61; MS m/z−254.8 (M−H)

Fuente