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

HRID 1616561

Reaction equation

HRID 1616561 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-35afd06486c941cd8b59766b9aa1429a
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Linked notes

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