تفاعل #2045070

معادلة التفاعل

DMF

13

5-Azido-8-hydroxy-2-methylquinoline

imidazole

tert-butyldiphenylsilyl chloride

→

protected product

5-Azido-8-tert-butyldiphenylsilyloxy-2-methylquinoline

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with aqueous HCl (0.1 M, 50 mL), brine (100 mL), water (100 mL)
2. 2
   تجفيفdried over Na2SO4
3. 3
   أخرىevaporated under reduced pressure

الإجراء التجريبي

A 100-mL flask was successively loaded with dry DMF (10 mL), 13 (200 mg, 1 mmol), imidazole (68.08 mg, 1 mmol), and tert-butyldiphenylsilyl chloride (302 mg, 1.1 mmol). The solution was stirred at room temperature for 10 h, diluted with ethyl acetate (500 mL), washed with aqueous HCl (0.1 M, 50 mL), brine (100 mL), water (100 mL), dried over Na2SO4 and evaporated under reduced pressure to afford 8.41 g (96%) of protected product as a colorless oil (428 mg, 98%). 1H NMR (500 MHz, CDCl3) δ ppm: 1.19 (s, 9H), 2.33 (s, 3H), 6.98 (d, J=8.5 Hz, 1H), 7.06 (d, J=8.5 Hz, 1H), 7.10 (d, J=8.5 Hz, 1H), 7.38-7.26 (m, 6H), 7.81-7.79 (m, 4H), 8.11 (d, J=8.5 Hz, 1H). 13C NMR (125 MHz, CDCl3) δ ppm: 20.1, 24.3, 26.8, 113.5, 116.7, 120.6, 121.8, 127.3, 128.4, 129.2, 130.6, 134.3, 135.1, 140.9, 148.9, 157.9. HRMS (ESI): calc'd for C26H26N4OSi [M+H]+: 438.1876, found: 438.1879.

المصدر