Hydrochloric Acid → 1-(2-Methyl-8-quinolyl)-2,3,4,5-tetramethylcyclopentadiene

HRID 896737

반응식

HRID 896737 반응식
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.[Li]CCCC.[CH3:18][C:19]1[C:20](=O)[CH:21]([CH3:26])[CH:22]([CH3:25])[C:23]=1[CH3:24].Cl>C1COCC1>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([C:20]3[CH:19]([CH3:18])[C:23]([CH3:24])=[C:22]([CH3:25])[C:21]=3[CH3:26])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 410922,3,4,5-Tetramethyl-2-cyclopentenoneHCID 47150308-Bromo-2-methylquinolineHCID 178418339Butyllithium

생성물 1

HCID 223521291-(2-Methyl-8-quinolyl)-2,3,4,5-tetramethylcyclopentadiene수율 60.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4.4 g of 8-bromo-2-methylquinoline (20 mmol) in 50 ml of THF was cooled to −78° C., and 8.8 ml of n-BuLi (2.5 M in hexane, 22 mmol) was added dropwise while stirring. After ten minutes of stirring, 3.5 g of 2,3,4,5-tetramethylcyclopentenone (25 mmol) was added dropwise; the solution was heated to room temperature and then heated in reflux for one hour. The solution was cooled down; ice and hydrochloric acid to approximately pH 1 were added; and after neutralization with ammonia solution, the phases were separated and the aqueous phase was extracted with pentane. The combined organic extracts were dried, the pentane was removed in a vacuum, and the remaining brown oil was distilled in a high vacuum (boiling point: 115° C. at 0.01 mbar). A 60% yield (3.2 g) of 1-(2-methyl-8-quinolyl)-2,3,4,5-tetramethylcyclopentadiene in the form of yellow, viscous oil was obtained.

후처리

  1. stirringAfter ten minutes of stirring
  2. temperatureheated
  3. temperaturein reflux for one hour
  4. temperatureThe solution was cooled down
  5. customand after neutralization with ammonia solution, the phases were separated
  6. extractionthe aqueous phase was extracted with pentane
  7. customThe combined organic extracts were dried
  8. customthe pentane was removed in a vacuum
  9. distillationthe remaining brown oil was distilled in a high vacuum (boiling point: 115° C. at 0.01 mbar)

출처 및 근거

ORD 기록
ord-dd7731bab6ef4a2db1c22a813597413c
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919412B1

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