Hydrochloric Acid → 4-Pentenoic acid, 5-(2-methylphenyl)-3-oxo-, eth

HRID 1610686노트

반응식

HRID 1610686 반응식
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[K+].[C:26]([O:32][CH2:33][CH3:34])(=[O:31])[CH2:27]C([O-])=O.[Cl-].[Mg+2].[Cl-].Cl>O1CCCC1.C(OCC)(=O)C.O>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1/[CH:4]=[CH:5]/[C:6](=[O:8])[CH2:27][C:26]([O:32][CH2:33][CH3:34])=[O:31]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 983063-(2-Methylphenyl)prop-2-enoic acidHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium Chloride

생성물 1

HCID 202607254-Pentenoic acid, 5-(2-methylphenyl)-3-oxo-, eth

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-methylcinnamic acid (50.71 g, 312.7 mmol) in tetrahydrofuran (500 ml) was added 1,1′-carbonyldiimidazole (55.8 g, 344 mmol) at room temperature, and the mixture was stirred as it was for 1 hr. To the mixture were added monoethyl malonate monopotassium salt (58.5 g, 344 mmol) and magnesium chloride (16.4 g, 172 mmol) at room temperature, and the mixture was stirred at 60° C. overnight. The reaction solution was diluted with ethyl acetate and water and acidified with conc. hydrochloric acid. The ethyl acetate layer was separated, and the aqueous layer was extracted with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-6/1) to give the objective substance.

후처리

  1. stirringthe mixture was stirred at 60° C. overnight
  2. customThe ethyl acetate layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate=9/1-6/1)
  8. customto give the objective substance

출처 및 근거

ORD 기록
ord-81577f415a874644b6da42e31ccf19a2
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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