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Hydrochloric Acid → 5,5,5-Trifluoro-2-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentanal

HRID 1669306
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HRID 1669306 반응식
[F:1][C:2]([F:26])([F:25])[CH2:3][CH2:4][C:5]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)=[CH:6][O:7]C.O1CCCC1.Cl.[OH-].[Na+]>C(OCC)C>[F:26][C:2]([F:1])([F:25])[CH2:3][CH2:4][CH:5]([C:9]1[CH:14]=[N:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH:6]=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 866203565-(4,4,4-Trifluoro-1-methoxymethylene-butyl)-2-(4-trifluoromethyl-phenyl)-pyridine

생성물 1

HCID 866203575,5,5-Trifluoro-2-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentanal수율 91.7%

시약·촉매·용매 1

HCID 3283
Diethyl Ether
용매

실험 절차

A solution of 5-(4,4,4-trifluoro-1-methoxymethylene-butyl)-2-(4-trifluoromethyl-phenyl)-pyridine (4.1 g, 10.9 mmol) and tetrahydrofuran (50 mL) is treated with concentrated hydrochloric acid (5 mL) and heated to reflux under nitrogen. The reaction is monitored by HPLC and allowed to cool upon completion. The solution is neutralized with 20% NaOH solution and diluted with diethyl ether. The two phases are separated and the organic layer washed with brine and water. The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated. Chromatography gives purified 5,5,5-trifluoro-2-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentanal (3.6 g, 10 mmol) 79% yield.

후처리

  1. temperatureheated
  2. temperatureto reflux under nitrogen
  3. temperatureto cool upon completion
  4. customThe two phases are separated
  5. washthe organic layer washed with brine and water
  6. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customChromatography gives

출처 및 근거

ORD 기록
ord-59c285660d7e4f79acbc03d30a922e5b
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07989457B2

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