Hydrazine hydrate (1:1) → (3,5-diethyl-1H-pyrazol-4-yl)acetic acid ethyl ester

HRID 549411Notes

Reaction equation

HRID 549411 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([C:11](=O)[CH2:12][CH3:13])[C:7](=O)[CH2:8][CH3:9])[CH3:2].O.[NH2:17][NH2:18]>C(O)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[C:11]([CH2:12][CH3:13])=[N:17][NH:18][C:7]=1[CH2:8][CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 50988004Ethyl 4-oxo-3-propanoylhexanoate

Product 1

HCID 57899303(3,5-diethyl-1H-pyrazol-4-yl)acetic acid ethyl esterYield 72.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-oxo-3-propionyl-hexanoic acid ethyl ester (15 g, 70 mmol) and hydrazine hydrate (3.5 mL, 71 mmol) in absolute ethanol (150 mL) was refluxed for 16 h. Solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (methanol in methylene chloride) to provide (3,5-diethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester as yellow oil (11 g, 51 mmol).

Workup

  1. temperaturewas refluxed for 16 h
  2. customSolvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (methanol in methylene chloride)

Sources & evidence

ORD record
ord-abe838f89a674b69a767ed887a8e3506
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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