1,1'-Carbonyldiimidazole → Imidazole-1-carboxylic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester

HRID 72326Notes

Reaction equation

HRID 72326 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][OH:21])[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](N1C=CN=C1)([N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1)=[O:23]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][O:21][C:22]([N:24]3[CH:28]=[CH:27][N:26]=[CH:25]3)=[O:23])[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 64164588[3-(4-Benzyloxy-phenyl)-isoxazol-5-yl]-methanol

Product 1

HCID 46892233Imidazole-1-carboxylic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methanol (500 mg, 1.77 mmol) was dissolved in 10 ml of THF, to which solution was added 1,1′-carbonyldiimidazole (576 mg, 3.55 mmol), and stirred at room temperature for 1 hour. The THF was distilled off under reduced pressure and extracted three times with water and ethyl acetate. An obtained organic layer was distilled under reduced pressure and recrystallized from hexane/ethyl acetate (1/4) conditions to obtain imidazole-1-carboxylic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester as a desired solid compound.

Workup

  1. distillationThe THF was distilled off under reduced pressure
  2. extractionextracted three times with water and ethyl acetate
  3. distillationAn obtained organic layer was distilled under reduced pressure
  4. customrecrystallized from hexane/ethyl acetate (1/4) conditions

Sources & evidence

ORD record
ord-f5596a5c395f423da4474741958ace3b
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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