تفاعل #68629

معادلة التفاعل

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

المردود 82.0%

المذيبات

—

hexanes

—

hexanes

EtOAc

EtOAc

Benzene

ظروف التفاعل

المعالجة

1. 1
   أخرىthen sealed with a septum
2. 2
   درجة الحرارةto warm to rt
3. 3
   درجة الحرارةmaintained 20 h
4. 4
   أخرىThe solution was then partitioned between saturated aqueous
5. 5
   أخرىNH4Cl, and the layers separated
6. 6
   استخلاصThe aqueous layer was extracted with EtOAc (2×50 mL)
7. 7
   غسيلthe combined organic layers were washed with brine
8. 8
   تجفيفdried (MgSO4)
9. 9
   تركيزconcentrated in vacuo
10. 10
    أخرىThe resulting residue was purified by MPLC (Teledine Isco combiFlash Companion), 80 g SiO2, solvent system

الإجراء التجريبي

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.

المصدر