1,3-Diethyl 2-(4-aminophenyl)propanedioate → 2-(4-Aminophenyl)propane-1,3-diol

HRID 28621노트

반응식

HRID 28621 반응식
C([O:3][C:4](=O)[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[C:6](OCC)=[O:7])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([CH:5]([CH2:6][OH:7])[CH2:4][OH:3])=[CH:16][CH:15]=1

참가 물질

4

반응물 2

HCID 124708371,3-Diethyl 2-(4-aminophenyl)propanedioateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 195939762-(4-Aminophenyl)propane-1,3-diol수율 17.3%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 2-(4-amino-phenyl)-malonic acid diethyl ester (450 mg, 1.8 mmol) in anhydrous ether (20 ml), cooled at 0-10° C., was added lithium aluminum hydride (68 mg, 1.8 mmol). After stirring at room temperature for 2 hours, the reaction was cooled to 10° C. and quenched by the addition of hydrated sodium sulfate (2 g). The mixture was filtered and the solid was rinsed with tetrahydrofuran (10 ml). The combined filtrates were concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 20% methanol-chloroform to provide 2-(4-amino-phenyl)-propane-1,3-diol (52 mg, 17% yield).

후처리

  1. temperaturethe reaction was cooled to 10° C.
  2. customquenched by the addition of hydrated sodium sulfate (2 g)
  3. filtrationThe mixture was filtered
  4. washthe solid was rinsed with tetrahydrofuran (10 ml)
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel eluting with 20% methanol-chloroform

출처 및 근거

ORD 기록
ord-3a5f2e55380a46d2918588bd06ad3564
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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