反应详情

温度

0 °C

To a suspension of tert-butyl 2-(3-hydroxyquinolin-6-yl)acetate (0.1 g, 0.4 mmol) in benzene (5 mL) was added methanol (0.05 ml, 1 mmol) and tributylphosphine (0.1 ml, 0.6 mmol). The resulting mixture was cooled to 0° C. followed by adding 1,1′-(azodicarbonyl)dipiperidine (0.1 g, 0.6 mmol). After 10 min, ice bath was removed; the reaction mixture was warmed up to rt. The reaction mixture was continued to stir for 20 h. TLC showed about 80% conversion. More MeOH (1 ml), tibutylphosphine (0.05 mL), and ADDP (50 mg) were added and allowed to stir for 3 h. Hexane was added to the reaction mixture and dihydro-ADDP separated out and was filtered off. The filtrate was concentrated. The crude product was purified using SiO2 chromatography (TELEDYNE ISCO REDISEP®, P/N 68-2203-027, 40 g SiO2) to afford the desired product as colorless liquid. MS m/z: 274.3 (M+H). Calc'd. for C16H19NO3−273.2.

1. customice bath was removed
2. temperaturethe reaction mixture was warmed up to rt
3. additionMore MeOH (1 ml), tibutylphosphine (0.05 mL), and ADDP (50 mg) were added
4. stirringto stir for 3 h
5. additionHexane was added to the reaction mixture and dihydro-ADDP
6. customseparated out
7. filtrationwas filtered off
8. concentrationThe filtrate was concentrated
9. customThe crude product was purified