반응 #94875

반응 방정식

butyl lithium

8-Bromo-6-chloroquinoline

diethyl oxalate

→

title product

Ethyl 2-(6-Chloro-8-quinolyl)-2-oxoacetate

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타held at -70° C
2. 2
   기타quenched at 0°-5° C. with glacial acetic acid (17 ml.) in 50 ml
3. 3
   온도After warming to room temperature the quenched mixture
4. 4
   workup.ADDITIONwas poured into 500 ml
5. 5
   workup.ADDITIONof water and then diluted with 500 ml
6. 6
   기타The organic layer was separated
7. 7
   세척washed with 500 ml
8. 8
   건조of fresh bicarbonate, dried over anhydrous magnesium sulfate
9. 9
   여과filtered
10. 10
    기타evaporated to an oil

실험 절차

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 ml. 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).

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