Acetic Acid → HCID 10691755, compound

HRID 1532748Notes

Reaction equation

HRID 1532748 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.[CH3:24][C:25](=[O:30])[CH2:26][C:27](=[O:29])[CH3:28].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:26]([C:25](=[O:30])[CH3:24])[C:27](=[O:29])[CH3:28])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

Product 1

HCID 10691755HCID 10691755, compoundYield 60%

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 2,4-pentanedione (1.2 g, 12 mmol), acetic acid (300 mg) and piperidine (425 mg). While removing water through Dean-Stark trap, the mixture was refluxed under heating. Five hours later, toluene was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=1:1) and the fraction containing the objective substance was concentrated under reduced pressure to give the title compound (2.3 g, yield 60%) as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-a60d625c40534a71ab51a73b99f7beb7
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

Loading…