Acetic Acid → HCID 22013889, compound

HRID 1532747Notes

Reaction equation

HRID 1532747 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:33][CH:34]([CH3:36])[CH3:35])(=[O:32])[CH2:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[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][CH:29]([CH3:31])[CH3:30])=[O:27])[C:24]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 83223Diisopropyl malonateHCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

Product 1

HCID 22013889HCID 22013889, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (3.07 g, 10 mmol) synthesized according to the method described in WO95/18125 in toluene (40 ml) were added diisopropyl malonate (1.88 g, 10 mmol), acetic acid (300 mg) and piperidine (425 mg). While removing water through Dean-Stark trap, the mixture was refluxed under heating. Eight hours later, toluene was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=75:25) and the fraction containing the objective substance was concentrated under reduced pressure to give the title compound (4.2 g, yield 88%) as a yellow oil.

Workup

  1. customWhile removing water through Dean-Stark trap
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating
  4. customEight hours later, toluene was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=75:25)
  6. additionthe fraction containing the objective substance
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-ecfa2bd806f941b0acffa5230ebdfe50
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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