Hydrochloric Acid → 2-{[4-(Trifluoromethyl)pyridin-2-yl]methylidene}cyclopentan-1-one

HRID 1750470노트

반응식

HRID 1750470 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=O)[CH:4]=1.[C:13]1(N2CCOCC2)[CH2:17][CH2:16][CH2:15][CH:14]=1.Cl.C(=O)(O)[O-:26].[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=[C:14]2[CH2:15][CH2:16][CH2:17][C:13]2=[O:26])[CH:4]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 702941-MorpholinocyclopenteneHCID 516892Sodium BicarbonateHCID 147614714-(Trifluoromethyl)pyridine-2-carbaldehyde

생성물 1

HCID 1317336082-{[4-(Trifluoromethyl)pyridin-2-yl]methylidene}cyclopentan-1-one

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

A solution of 4-(trifluoromethyl)pyridine-2-carbaldehyde (CAS number 132470-83-8; 1.00 g, 5.71 mmol) and 4-(cyclopent-1-en-1-yl)morpholine (CAS number 936-52-7; 0.90 ml, 5.60 mmol) in toluene (15 ml) was heated at 90° C. for 18 hours. The reaction was then cooled to room temperature and concentrated HCl (2 ml) and water (2 ml) was added drop wise. The reaction was stirred at room temperature for 20 minutes and then neutralised with a saturated solution of sodium bicarbonate and then basified with 2 M NaOH (aq). The organics were extracted with ethyl acetate (2×40 ml) and the combined organics were washed with brine (10 ml), dried over magnesium sulfate, filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol) to afford the title compound.

후처리

  1. extractionThe organics were extracted with ethyl acetate (2×40 ml)
  2. washthe combined organics were washed with brine (10 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered through a hydrophobic frit
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol)

출처 및 근거

ORD 기록
ord-427dcf0738884ed2a51247ed93331a6b
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156829B2

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