Reaktion #2045070

Reaktionsgleichung

DMF

13

5-Azido-8-hydroxy-2-methylquinoline

imidazole

tert-butyldiphenylsilyl chloride

→

protected product

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

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with aqueous HCl (0.1 M, 50 mL), brine (100 mL), water (100 mL)
2. 2
   Trocknendried over Na2SO4
3. 3
   Sonstigeevaporated under reduced pressure

Vorschrift

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.

Quelle