Diethyl Malonate → HCID 12369938, compound

HRID 732956Notes

Reaction equation

HRID 732956 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:14]=1[CH:15]=O>C1(C)C=CC=CC=1.N1CCCCC1.C(O)(=O)C>[Cl:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:14]=1[CH:15]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 2

HCID 7761Diethyl MalonateHCID 134042,4-Dichlorobenzaldehyde

Product 1

HCID 12369938HCID 12369938, compoundYield 101%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of diethyl malonate (0.92 g, 5.71 mmol) in toluene (10 mL) was added 2,4-dichlorobenzaldehyde (1 g, 5.71 mmol), piperidine (23 μL, 0.23 mmol), acetic acid (13 μL, 0.23 mmol) and molecular sieves (3 Å). The reaction was heated to 70° C. for 2 days and was concentrated under reduced pressure. The residue was filtered through a pad of silica flushing with EtOAc/hexane (1:1) solution. The filtrate was concentrated to give diethyl 2-(2,4-dichlorobenzylidene)malonate (1.83 g, 97%) as a yellow oil.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. filtrationThe residue was filtered through a pad of silica flushing with EtOAc/hexane (1:1) solution
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7be6e7b7cf6040daad83b0783c5710ea
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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