Isopropyl iodide → methyl 1-isopropyl-1H-imidazole-4-carboxylate

HRID 2355288노트

반응식

HRID 2355288 반응식
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][NH:10][CH:11]=1)=[O:6].[CH:12](I)([CH3:14])[CH3:13]>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][N:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=1)=[O:6]

참가 물질

5

반응물 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 178418785HCID 178418785, 화합물

생성물 1

HCID 20769004methyl 1-isopropyl-1H-imidazole-4-carboxylate수율 17.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Add sodium hydride (2.87 g, 71.7 mmol, 60% in mineral oil) portion-wise over 10 minutes to a cooled (0° C.) solution of 1H-imidazole-4-carboxylic acid methyl ester (6.03 g, 47.8 mmol) in dimethylformamide (150 ml). Remove the cooling bath and stir at room temperature for 4.5 hrs. Cool the mixture to 0° C. and add isopropyl iodide (8.94 g, 52.6 mmol) dropwise over 10 min. Remove the cooling bath and stir at room temperature for 20 hrs. Quench the mixture with saturated aqueous ammonium chloride and extract with ethyl acetate (3×). Wash the combined extracts with brine, dry over sodium sulfate, filter and concentrate under reduced pressure to give an oil. Purify the oil by flash chromatography (silica gel) eluting with 25% acetone/hexanes to provide the product as an oil (1.41 g, 8.4 mmol, 17% yield). M/S (m/z): 169 (M+H).

후처리

  1. customRemove the cooling bath
  2. temperatureCool the mixture to 0° C.
  3. customRemove the cooling bath
  4. stirringstir at room temperature for 20 hrs
  5. customQuench the mixture with saturated aqueous ammonium chloride
  6. extractionextract with ethyl acetate (3×)
  7. washWash the combined extracts with brine
  8. dry with materialdry over sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate under reduced pressure
  11. customto give an oil
  12. customPurify the oil by flash chromatography (silica gel)
  13. washeluting with 25% acetone/hexanes

출처 및 근거

ORD 기록
ord-aabb3aa26c8347adafa521581d27e637
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754742B2

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