Tetrahydrofuran → Methyl 2-(acetylthio)-4-bromobutanoate

온도

-20 °C

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)

1. wait0° C. for 2 hours under Ar
2. concentrationthe mixture was concentrated
3. additiondiluted with EtAc/Hexane
4. washwashed with 1.0 M NaH2PO4
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customSiO2 chromatographic purification (1:12 to 1:10 EtAc/Hexane)

ORD 기록

ord-d0633b1a8d424c299d1fbced2d978c76

출처 데이터셋

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08236319B2