反应 #969846

反应方程式

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

thioacetic acid

DIPEA

→

title compound

收率 90.0%

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

收率 90.0%

溶剂

THF

THF

反应条件

后处理

1. 1
   其他evaporated
2. 2
   workup.DISSOLUTIONThe mixture was redissolved in methanol
3. 3
   过滤filtered through celite,
4. 4
   浓缩concentrated
5. 5
   其他purified with SiO2 chromatography
6. 6
   洗涤eluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1)

实验过程

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)

来源