تفاعل #969844

معادلة التفاعل

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

thioacetic acid

DIPEA

→

title compound

المردود 90.0%

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

المردود 90.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىevaporated
2. 2
   workup.DISSOLUTIONThe mixture was redissolved in methanol
3. 3
   ترشيحfiltered through celite,
4. 4
   تركيزconcentrated
5. 5
   أخرىpurified with SiO2 chromatography
6. 6
   غسيلeluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1)

الإجراء التجريبي

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)

المصدر