Diethyl Malonate → Diethyl 2-(3-methyl-2-nitrobenzylidene)malonate

HRID 1435937Notes

Reaction equation

HRID 1435937 reaction equation
[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:13]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 516892Sodium BicarbonateHCID 135735673-Methyl-2-nitrobenzaldehyde

Product 1

HCID 68898055Diethyl 2-(3-methyl-2-nitrobenzylidene)malonateYield 90.8%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of this aldehyde (10.0 g, 60.6 mmol) in 20 mL of acetic anhydride was added diethyl malonate (9.7 g, 60.6 mmol) and sodium bicarbonate (7.6 g, 91 mmol). The reaction mixture was stirred at 100° C. for 24 h. The reaction was allowed to cool and then was partitioned between ethyl acetate and water. The organics were washed sequentially with water, aq sat'd NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford 16.9 g (90%) of the title compound.

Workup

  1. temperatureto cool
  2. customwas partitioned between ethyl acetate and water
  3. washThe organics were washed sequentially with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5ad771bd5b564352bf233dcaab2d6fed
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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