Реакция #969845

Уравнение реакции

thiolacetic acid

DIPEA

THF

methyl 2,4-dibromobutanoate

THF

→

title compound

Выход 96.0%

Methyl 2-(acetylthio)-4-bromobutanoate

Выход 96.0%

Условия реакции

Обработка

1. 1
   workup.WAIT0° C. for 2 hours under Ar
2. 2
   Концентрированиеthe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with EtAc/Hexane
4. 4
   Промывкаwashed with 1.0 M NaH2PO4
5. 5
   Сушкаdried over MgSO4
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated
8. 8
   ДругоеSiO2 chromatographic purification (1:12 to 1:10 EtAc/Hexane)

Методика

10.0 g (38.4 mmol) of methyl 2,4-dibromobutanoate in 100 ml of dry THF at −20° C. was added dropwise 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)

Источник