Hydrochloric Acid → ethyl 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetate

HRID 1295244Notes

Reaction equation

HRID 1295244 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][C:14]#N)[C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:24].[Na+].[O:26]1CC[CH2:28][CH2:27]1.Cl>C(O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][C:14]([O:26][CH2:27][CH3:28])=[O:24])[C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 693145121-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile

Product 1

HCID 69422631ethyl 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetateYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile (13.0 g), 4N aqueous sodium hydroxide solution (100 ml), tetrahydrofuran (100 ml) and ethanol (100 ml) was refluxed for 3 days. After cooling, the mixture was neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. A mixture of the residue, ethyl iodide (5.2 ml), potassium carbonate (11.9 g) and N,N-dimethylformamide (100 ml) was stirred at room temperature for 3 hrs. The reaction solution was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetate (14.9 g, yield 99%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Workup

  1. temperaturewas refluxed for 3 days
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. additionA mixture of the residue, ethyl iodide (5.2 ml), potassium carbonate (11.9 g) and N,N-dimethylformamide (100 ml)
  8. additionThe reaction solution was poured into water
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-1bd52a7fd614467eb1dbd7d4a8394be4
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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