Réaction #969844

Équation de réaction

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

thioacetic acid

DIPEA

→

title compound

Rendement 90.0%

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

Rendement 90.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Autreevaporated
2. 2
   workup.DISSOLUTIONThe mixture was redissolved in methanol
3. 3
   Filtrationfiltered through celite,
4. 4
   Concentrationconcentrated
5. 5
   Autrepurified with SiO2 chromatography
6. 6
   Lavageeluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1)

Mode opératoire

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 being 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)

Source