Imidazole → Methyl 5-imidazol-1-ylpentanoate

HRID 870576ノート

反応式

HRID 870576 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 54266609Methyl 5-imidazol-1-ylpentanoate収率 82%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-493bd287764e44009cf038a93acdf5c0
出典データセット
uspto-grants-2015_03
特許番号
US08969555B2

反応ノート

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