Reaction #969846

Reaction equation

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

thioacetic acid

DIPEA

→

title compound

Yield 90.0%

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

Yield 90.0%

Solvents

THF

THF

Conditions

Workup

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

Procedure

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)

Source