반응 #969846

반응 방정식

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

thioacetic acid

DIPEA

→

title compound

수율 90.0%

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

수율 90.0%

용매

THF

THF

반응 조건

후처리

1. 1
   기타evaporated
2. 2
   workup.DISSOLUTIONThe mixture was redissolved in methanol
3. 3
   여과filtered through celite,
4. 4
   농축concentrated
5. 5
   기타purified with SiO2 chromatography
6. 6
   세척eluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1)

실험 절차

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)

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