Reaktion #969843

Reaktionsgleichung

thiolacetic acid

DIPEA

THF

methyl 2,4-dibromobutanoate

THF

→

title compound

Ausbeute 96.0%

Methyl 2-(acetylthio)-4-bromobutanoate

Ausbeute 96.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAIT0° C. for 2 hours under Ar
2. 2
   Einengenthe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with EtAc/Hexane
4. 4
   Waschenwashed with 1.0 M NaH2PO4
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeSiO2 chromatographic purification (1:12 to 1:10 EtAc/Hexane)

Vorschrift

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)

Quelle