반응 #68629

반응 방정식

di-tert-butyl azodicarboxylate

tert-butyl 2-(3-hydroxyquinolin-6-yl)acetate

triphenylphosphine

2-methoxyethanol

→

tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetate

수율 82.0%

용매

—

hexanes

—

hexanes

EtOAc

EtOAc

Benzene

반응 조건

후처리

1. 1
   기타then sealed with a septum
2. 2
   온도to warm to rt
3. 3
   온도maintained 20 h
4. 4
   기타The solution was then partitioned between saturated aqueous
5. 5
   기타NH4Cl, and the layers separated
6. 6
   추출The aqueous layer was extracted with EtOAc (2×50 mL)
7. 7
   세척the combined organic layers were washed with brine
8. 8
   건조dried (MgSO4)
9. 9
   농축concentrated in vacuo
10. 10
    기타The resulting residue was purified by MPLC (Teledine Isco combiFlash Companion), 80 g SiO2, solvent system

실험 절차

A flask was charged with tert-butyl 2-(3-hydroxyquinolin-6-yl)acetate (581.04 mg, 2.241 mmol) and triphenylphosphine (1.175 g, 4.482 mmol) then sealed with a septum and an placed under N2. Benzene (10 mL) was added, followed by 2-methoxyethanol (0.8838 ml, 11.20 mmol). The heterogeneous solution was cooled to 0° C., and di-tert-butyl azodicarboxylate (1.032 g, 4.482 mmol) was added as a solid in a single portion. The solution was allowed to warm to rt and maintained 20 h. The solution was then partitioned between saturated aqueous. NH4Cl, and the layers separated. The aqueous layer was extracted with EtOAc (2×50 mL), and the combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by MPLC (Teledine Isco combiFlash Companion), 80 g SiO2, solvent system: 90:10 hexanes:EtOAc gradient to 50:50 hexanes:EtOAc to give tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetate (585. 2 mg, 82% yield). LRMS (ESI) m/z calcd for C18H24NO4 (M+H) 318.2. found 318.3.

출처