Hydrochloric Acid → Diethyl 2-(3-(trifluoromethyl)pyridin-2-yl)malonate

HRID 1907677

반응식

HRID 1907677 반응식
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=1.Cl>O1CCOCC1.[Cu](Cl)Cl.C(OCC)(=O)C.O>[F:22][C:21]([F:24])([F:23])[C:20]1[C:15]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])=[N:16][CH:17]=[CH:18][CH:19]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

생성물 1

HCID 57950213Diethyl 2-(3-(trifluoromethyl)pyridin-2-yl)malonate수율 27.4%

시약·촉매·용매 4

HCID 24014Cupric Chloride촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매2회

실험 절차

8.73 g of sodium hydride (55% oil dispersion) was suspended in 100 ml of 1,4-dioxane. Into this, 32.03 g of diethyl malonate was added dropwise over a period of about 1 hour at 60° C. under a nitrogen atmosphere. The mixture was stirred further for 0.5 hours at the same temperature, then, 8.26 g of copper chloride (I) was added to the mixture. Thereafter, into the mixture, a solution prepared by dissolving 15.00 g of 2-chloro-3-(trifluoromethyl)pyridine in 50 ml of 1,4-dioxane at 80° C. was dropped. The mixture was stirred for 16 hours under reflux with heating. The reaction mixture was allowed to cool to room temperature, and to the reaction mixture was added 15 ml of concentrated hydrochloric acid. To the mixture were added water and ethyl acetate, and the mixture was filtrated through celite. The filtrate was liquid-separated. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 51.14 g of the resultant residue was subjected to silica gel column chromatography, to obtain 6.90 g of diethyl (3-trifluoromethyl-2-pyridyl)malonate.

후처리

  1. customThereafter, into the mixture, a solution prepared
  2. additionwas dropped
  3. stirringThe mixture was stirred for 16 hours
  4. temperatureunder reflux
  5. temperaturewith heating
  6. filtrationthe mixture was filtrated through celite
  7. customThe filtrate was liquid-separated
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c664465c17ad4d7dbb08de2c0cb69feb
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598176B2

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