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

HRID 1610686ノート

反応式

HRID 1610686 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-81577f415a874644b6da42e31ccf19a2
出典データセット
uspto-grants-2006_01
特許番号
US06982348B2

反応ノート

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