Réaction #969843

Équation de réaction

thiolacetic acid

DIPEA

THF

methyl 2,4-dibromobutanoate

THF

→

title compound

Rendement 96.0%

Methyl 2-(acetylthio)-4-bromobutanoate

Rendement 96.0%

Conditions de réaction

Traitement

1. 1
   workup.WAIT0° C. for 2 hours under Ar
2. 2
   Concentrationthe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with EtAc/Hexane
4. 4
   Lavagewashed with 1.0 M NaH2PO4
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated
8. 8
   AutreSiO2 chromatographic purification (1:12 to 1:10 EtAc/Hexane)

Mode opératoire

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)

Source