反应 #969843

反应方程式

thiolacetic acid

DIPEA

THF

methyl 2,4-dibromobutanoate

THF

→

title compound

收率 96.0%

Methyl 2-(acetylthio)-4-bromobutanoate

收率 96.0%

反应条件

后处理

1. 1
   workup.WAIT0° C. for 2 hours under Ar
2. 2
   浓缩the mixture was concentrated
3. 3
   workup.ADDITIONdiluted with EtAc/Hexane
4. 4
   洗涤washed with 1.0 M NaH2PO4
5. 5
   干燥dried over MgSO4
6. 6
   过滤filtered
7. 7
   其他evaporated
8. 8
   其他SiO2 chromatographic purification (1:12 to 1:10 EtAc/Hexane)

实验过程

10.0 g (38.4 mmol) of methyl 2,4-dibromobutanoate in 100 ml of dry THF at 20° C. was added drop wise the mixture of 2.75 ml (38.5 mmol) of thiolacetic acid in 8.5 ml (48.9 mmol) of DIPEA and 50 ml of dry THF in 1.5 hour. After stirring overnight at −20° C. then 0° C. for 2 hours under Ar, the mixture was concentrated, diluted with EtAc/Hexane, washed with 1.0 M NaH2PO4, dried over MgSO4, filtered, evaporated, and SiO2 chromatographic purification (1:12 to 1:10 EtAc/Hexane) to afford 9.5 g (96%) of the title compound. 1H NMR (CDCl3) 4.38 (1H, t, J=7.1 Hz), 3.74 (s, 3H), 3.40 (m, 2H), 2.57˜2.47 (m, 1H), 2.37 (s, 3H), 2.36˜2.21 (m, 1H); 13C NMR 193.24, 171.36, 53.15, 44.45, 34.67, 30.46, 29.46; MS m/z+276.9 (M+Na), 278.9 (M+2+Na)

来源