1,3-Diethyl 2-oxopropanedioate → Diethyl 2-(2-methyl-2-propionylhydrazono)malonate

HRID 15964

Reaction equation

HRID 15964 reaction equation
[CH3:1][N:2]([C:4](=[O:7])[CH2:5][CH3:6])[NH2:3].O=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:4](=[O:7])[CH2:5][CH3:6])[N:3]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 542680N-methylpropionohydrazide

Product 1

HCID 57442166Diethyl 2-(2-methyl-2-propionylhydrazono)malonateYield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-methylpropionohydrazide (18.78 g, 183.9 mmol) and diethyl ketomalonate (56.1 mL, 368 mmol) in toluene (136 mL) was refluxed with a Dean-Stark trap for 4 hours. The reaction mixture was concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (100% hexanes to 5 to 10% EtOAc in hexanes) to afford 23 g (49%) of the desired product.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give the crude material that
  3. customwas purified by silica gel flash column chromatography (100% hexanes to 5 to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5cdca83ee7f64971b5c07200968b6b9d
Source dataset
uspto-grants-2010_06
Patent number
US07732616B2

Linked notes

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