Diethyl Malonate → HCID 10551486, compound

HRID 1532749Notes

Reaction equation

HRID 1532749 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.[C:24]([O:32][CH2:33][CH3:34])(=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].N1CCCCC1>C(O)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:24]([O:32][CH2:33][CH3:34])=[O:31])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

Product 1

HCID 10551486HCID 10551486, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (8.0 g, 26.0 mmol) synthesized according to the method described in WO95/18125, diethyl malonate (4.79 g, 29.9 mmol), acetic acid (1.04 ml) and piperidine (1.03 ml) were mixed. While removing water through Dean-Stark trap, the mixture was refluxed under heating. Three and a half hours later, toluene was evaporated and the obtained residue was recrystallized from ethyl acetate-hexane to give the title compound (9.55 g, yield 82%) as pale-brown white crystals.

Workup

  1. additionwere mixed
  2. customWhile removing water through Dean-Stark trap
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating
  5. customThree and a half hours later, toluene was evaporated
  6. customthe obtained residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1677ebc478f44b1aa4bc611119d093b9
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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