反应详情

温度

0 °C

8-Bromo-6-chloroquinoline [J. Het. Chem. 6, pp. 243-245 (1969); 6 g., 0.025 mole]in 50 ml. of tetrahydrofuran was added dropwise over a 10 minute period to a mixture of butyl lithium (2.3 M in hexane, 12.2 ml., 0.028 mole) and 40 ml. of tetrahydrofuran held at -70° C. After an additional 30 minutes at this temperature, a cold (0° C.) solution of diethyl oxalate (14.6 g, 0.10 mole) in 50 ml. of tetrahydrofuran was added dropwise. The reaction mixture was maintained at 0° C. for 1 hour, then quenched at 0°-5° C. with glacial acetic acid (17 ml.) in 50 ml. of tetrahydrofuran. After warming to room temperature the quenched mixture was poured into 500 m1. of water and then diluted with 500 ml. of ethyl acetate and 500 ml. of saturated sodium bicarbonate. The organic layer was separated, washed with 500 ml. of fresh bicarbonate, dried over anhydrous magnesium sulfate, filtered, and evaporated to an oil. Trituration with two 100 ml. portions of hexane gave the title product (2.3 g., m.p. 107°-110° C.; m/e 265/263).

1. customheld at -70° C
2. customquenched at 0°-5° C. with glacial acetic acid (17 ml.) in 50 ml
3. temperatureAfter warming to room temperature the quenched mixture
4. additionwas poured into 500 m1
5. additionof water and then diluted with 500 ml
6. customThe organic layer was separated
7. washwashed with 500 ml
8. dry with materialof fresh bicarbonate, dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. customevaporated to an oil