反応 #4881
ord-b3282ab649924efeb49346007aa7bf75
反応方程式
反応条件
後処理
- 1温度while maintaining the temperature at -60° to -70° C
- 2workup.ADDITIONSubsequent to this addition
- 3温度while maintaining the temperature at -60° to -70° C
- 4その他at -65° C.
- 5その他for 20 minutes
- 6workup.ADDITIONsubsequent to this addition
- 7その他the entire reaction mixture
- 8その他Most of the solvent was evaporated in a stream of air
- 9その他the residual solvent was removed by rotary evaporation
- 10洗浄washed with 3×50 ml of isopropyl ether
- 11ろ過The aqueous layer was filtered
- 12その他The precipitate was collected
- 13洗浄washed with water, isopropyl alcohol, and isopropyl ether
- 14その他dried
実験手順
To a solution of 21.3 ml (0.15 mole) of diisopropyl amine in 300 ml of dry tetrahydrofuran under a continuous nitrogen blanket, at -70° C., was added 61.6 ml of 2.7M n-butyllithium in hexane (0.165 mole) while maintaining the temperature at -60° to -70° C. Subsequent to this addition, the temperature was maintained at -65° C. for approximately 20 minutes. A solution of 20 g (0.12 mole) of 2-chloroquinoline in 60 ml of tetrahydrofuran was added dropwise while maintaining the temperature at -60° to -70° C. After holding the temperature at -65° C. for 20 minutes subsequent to this addition, the entire reaction mixture was poured onto a large excess of dry ice. Most of the solvent was evaporated in a stream of air; the residual solvent was removed by rotary evaporation. The residue was taken up in 300 ml water, made basic with dil aq. sodium hydroxide and washed with 3×50 ml of isopropyl ether. The aqueous layer was filtered and made acidic (4 to 5 pH) with dilute aqueous hydrochloric acid. The precipitate was collected, washed with water, isopropyl alcohol, and isopropyl ether, and dried, giving 15.4 g (62%) of white crystals, m.p. 190°-210° C. (decomp.). A sample was recrystallized from isopropyl alcohol giving an analytical sample, m.p. 190°-210° C. (decomp.).