反応 #969844

反応方程式

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

thioacetic acid

DIPEA

→

title compound

収率 90.0%

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

収率 90.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   その他evaporated
2. 2
   workup.DISSOLUTIONThe mixture was redissolved in methanol
3. 3
   ろ過filtered through celite,
4. 4
   濃縮concentrated
5. 5
   その他purified with SiO2 chromatography
6. 6
   洗浄eluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1)

実験手順

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)

出典