Diethyl Malonate → HCID 21845282, compound

HRID 2259530Notes

Reaction equation

HRID 2259530 reaction equation
[I:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[C:7](O)[C:6]=1[O:14][CH2:15][CH2:16][I:17].[C:18]([O:26]CC)(=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>N1CCCCC1.C(O)C>[I:17][CH2:16][CH2:15][O:14][C:6]1[CH:7]=[C:8]2[C:11](=[CH:12][C:5]=1[O:4][CH2:3][CH2:2][I:1])[O:26][C:18](=[O:25])[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:9]2

Participants

5

Reactant 2

HCID 7761Diethyl MalonateHCID 86749140HCID 86749140, compound

Product 1

HCID 21845282HCID 21845282, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To 1.73 g (10.8 mmol) of the bis-iodoethoxyhydroxybenzaldehyde from Example 8 was added diethyl malonate, 2.1 g (4.6 mmol), and this mixture was heated on a steam bath. When the mixture had become homogeneous, two drops of piperidine were added. After the mixture had cooled, a precipitate formed. The solution was diluted with a few milliliters of ethanol and reheated to boiling on the steam bath. After the solution had cooled, it was filtered and the precipitate product retained. The product was a solid with a m.p. of 162°-165° C. Proton NMR confirmed the structure of the product.

Workup

  1. temperaturethis mixture was heated on a steam bath
  2. temperatureAfter the mixture had cooled
  3. customa precipitate formed
  4. temperatureAfter the solution had cooled
  5. filtrationit was filtered

Sources & evidence

ORD record
ord-f77381e7d3154b109068227f4b69e3f8
Source dataset
uspto-grants-1995_12
Patent number
US05474743

Reaction notes

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