Formic Acid → 4-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

HRID 4409

Reaction equation

HRID 4409 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]([C:20]#N)=[CH:18][CH:17]=1.C(O)=[O:25]>[Ni]>[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:25])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 137139704-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzonitrile

Product 1

HCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehydeYield 78.5%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzonitrile (6.5 g), Raney nickel alloy (6.5 g) and 70% formic acid (100 ml) was heated under reflux for 2 hours. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The remaining oily material was chromatographed on a column of silica gel, and from the fractions eluted with chloroform-hexane (1:1, V/V), there were obtained crystlas (5.2 g, 78.5%) of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde. Recrystallization from ether-hexane yielded colorless needles, m.p. 82°-84° C. Elemental analysis for C19H17NO3 ; Calcd.: C, 74.25; H, 5.57; N, 4.56. Found: C, 74.47; H, 5.53; N, 4.34.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe remaining oily material was chromatographed on a column of silica gel
  11. washfrom the fractions eluted with chloroform-hexane (1:1, V/V)

Sources & evidence

ORD record
ord-02ae9b80d0de45e4bc6c27c8e8753812
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Linked notes

Loading…