Реакция #969844

Уравнение реакции

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

thioacetic acid

DIPEA

→

title compound

Выход 90.0%

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

Выход 90.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Другоеevaporated
2. 2
   workup.DISSOLUTIONThe mixture was redissolved in methanol
3. 3
   Фильтрацияfiltered through celite,
4. 4
   Концентрированиеconcentrated
5. 5
   Другоеpurified with SiO2 chromatography
6. 6
   Промывкаeluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1)

Методика

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)

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