1,1'-Carbonyldiimidazole → Ethyl 6-(1-imidazolyl)-3-oxohexanoate

HRID 964583노트

반응식

HRID 964583 반응식
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:4][N:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:24]([O:26][C:27](=[O:32])[CH2:28]C(O)=O)[CH3:25]>O1CCCC1>[CH2:24]([O:26][C:27](=[O:32])[CH2:28][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[CH3:25]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 70615Monoethyl malonateHCID 3055390Imidazole-1-butyric acid

생성물 1

HCID 22097627Ethyl 6-(1-imidazolyl)-3-oxohexanoate수율 44%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 4-(1-imidazolyl)butyric acid (0.5 g) in tetrahydrofuran (35 ml), 1,1'-carbonyldiimidazole (0.578 g) was added, followed by stirring at room temperature for 6 hours. After magnesium salt of malonic acid monoethyl ester [Mg(OCOCH2COOC2H5)2 ] (1.02 g) was added, the mixture was stirred at room temperature for 18 more hours. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in dichloromethane. The dichloromethane layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residual oily substance was subjected to silica gel column chromatography and eluted with chloroform-methanol (30:1, v/v) to yield 6-(1-imidazolyl)-3-oxohexanoic acid ethyl ester (0.32 g, 44%) as an oily substance.

후처리

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 18 more hours
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washThe dichloromethane layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationafter which the solvent was distilled off
  8. washeluted with chloroform-methanol (30:1

출처 및 근거

ORD 기록
ord-3bbe189927fc4c66aa0e05d54c9d5a27
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770602

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