Sodium hydride → 8-[4-(2-Isopropoxyphenyl)imidazol-1-yl]octanoic acid methyl ester

HRID 1039175

反応式

HRID 1039175 の反応式
[H-].[Na+].[CH:3]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:14]=[CH:15][NH:16][CH:17]=1)([CH3:5])[CH3:4].[CH3:18][O:19][C:20](=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:18][O:19][C:20](=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:16]1[CH:17]=[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH:3]([CH3:5])[CH3:4])[N:14]=[CH:15]1

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 11107373Methyl 8-bromooctanoateHCID 1784582854-[2-(propan-2-yloxy)phenyl]-1H-imidazole

生成物 1

HCID 591678008-[4-(2-Isopropoxyphenyl)imidazol-1-yl]octanoic acid methyl ester収率 57.6%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Add sodium hydride (1.82 g, 38 mmol) to a suspension of 4-(2-isopropoxyphenyl)-1H-imidazole (5.01 g, 25 mmol) in THF (125 mL) at 0° C. under nitrogen, and warm the mixture to room temperature and stir for 1 hour. Cool the mixture to 0° C. and add 8-bromooctanoic acid methyl ester (5.98 g, 25 mmol) and tetra-n-butylammonium iodide (0.55 g, 1.5 mmol) and warm the mixture to room temperature to stir for 8 hours. Dilute the mixture with water (20 mL) and remove the solvent under reduced pressure. Dilute the residue with ethyl acetate (300 mL), wash with water (100 mL) and brine (100 mL), dry over sodium sulfate, and remove the solvent under reduced pressure to provide 8-[4-(2-isopropoxyphenyl)imidazol-1-yl]octanoic acid methyl ester (5.16 g, 57%), which is used in the next step without further purification.

後処理

  1. temperatureCool the mixture to 0° C.
  2. temperaturewarm the mixture to room temperature
  3. stirringto stir for 8 hours
  4. customremove the solvent under reduced pressure
  5. additionDilute the residue with ethyl acetate (300 mL)
  6. washwash with water (100 mL) and brine (100 mL)
  7. dry with materialdry over sodium sulfate
  8. customremove the solvent under reduced pressure

出典と根拠

ORDレコード
ord-e0df51e4888b4c41a02e544426edd101
出典データセット
uspto-grants-2013_10
特許番号
US08552039B2

関連ノート

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