تفاعل #969845

معادلة التفاعل

thiolacetic acid

DIPEA

THF

methyl 2,4-dibromobutanoate

THF

→

title compound

المردود 96.0%

Methyl 2-(acetylthio)-4-bromobutanoate

المردود 96.0%

ظروف التفاعل

المعالجة

1. 1
   workup.WAIT0° C. for 2 hours under Ar
2. 2
   تركيزthe mixture was concentrated
3. 3
   workup.ADDITIONdiluted with EtAc/Hexane
4. 4
   غسيلwashed with 1.0 M NaH2PO4
5. 5
   تجفيفdried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated
8. 8
   أخرىSiO2 chromatographic purification (1:12 to 1:10 EtAc/Hexane)

الإجراء التجريبي

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)

المصدر