Pentenone → ethyl 4,5-dihydro-3,5-dimethyl-1H-pyrazole-1-acetate

HRID 1916445

Reaction equation

HRID 1916445 reaction equation
Cl.[NH:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH2:3].[CH3:10][C:11](=O)[CH:12]=[CH:13][CH3:14].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:10][C:11]1[CH2:12][CH:13]([CH3:14])[N:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:3]=1

Participants

5

Reactant 3

HCID 12248PentenoneHCID 516892Sodium BicarbonateHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 67378927ethyl 4,5-dihydro-3,5-dimethyl-1H-pyrazole-1-acetateYield 14.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl hydrazinoacetate hydrochloride (1.55 g, 10 mmol), 3-pentene-2-one (0.95 mL, 10 mmol) and sodium bicarbonate (1.00 g, 11.9 mmol) in ethanol (10 mL) was stirred at room temperature overnight. The reaction mixture was then filtered and concentrated under reduced pressure. The resulting oil was purified by medium pressure liquid chromatography on silica gel (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a yellow oil (0.26 g).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting oil was purified by medium pressure liquid chromatography on silica gel (0 to 100% gradient of ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-cef1dd2f91c74bdc98647778372a4bf9
Source dataset
uspto-grants-2013_12
Patent number
US08618137B2

Linked notes

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