Imidazole → Methyl 5-imidazol-1-ylpentanoate

HRID 870576노트

반응식

HRID 870576 반응식
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].O>CN(C)C=O>[N:3]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:6][N:5]=[CH:4]1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 79557Methyl 5-bromovalerate

생성물 1

HCID 54266609Methyl 5-imidazol-1-ylpentanoate수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Add sodium hydride (0.212 g; 1.2 equiv; 5.29 mmoles) to a solution of 1H-imidazole (0.30 g; 1.0 equiv; 4.41 mmoles) and methyl 5-bromopentanoate (1.03 g; 1.2 equiv; 5.29 mmoles) in dimethylformamide (20 mL). Stir the mixture for 18 hours then add water (15 mL). Extract the mixture with dichloromethane and wash with brine (20 mL). Dry the organic phase over sodium sulfate, filter, and concentrate to give the crude product, which is purified by column chromatography (0 to 10% methanol in dichloromethane) to afford methyl 5-imidazol-1-ylpentanoate (0.655 g; 82%) as a yellow oil: MS (m/z): 183(M+1).

후처리

  1. extractionExtract the mixture with dichloromethane
  2. washwash with brine (20 mL)
  3. dry with materialDry the organic phase over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto give the crude product, which
  7. customis purified by column chromatography (0 to 10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-493bd287764e44009cf038a93acdf5c0
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969555B2

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