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

HRID 1440231Notes

Reaction equation

HRID 1440231 reaction equation
[C:1]1([C:7]2[O:8][C:9]([CH3:23])=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]#N)=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)=[O:25]>[Ni]>[C:1]1([C:7]2[O:8][C:9]([CH3:23])=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:22]=[CH:21][C:18]([CH:19]=[O:25])=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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]benzaldehyde

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 6.0 g of 4-(2-phenyl-5-methyloxazol4-ylethoxy)benzonitrile (prepared by reacting p-fluorobenzonitrile with 2-phenyl-4-hydroxyethyl-5-methyloxazole), 6.0 g of Raney nickel alloy and 100 ml of 70% formic acid was heated to reflux for 2 hours. The reaction was cooled and the solids filtered and washed with ethyl acetate. The washings and formic acid filtrate were combined and concentrated in vacuo to an oil. The residue was treated with water (100 ml) and extracted with ethyl acetate (3×100 ml). The extracts were combined and washed with water until the pH of the washings was 7. The extracts were washed with a brine solution, dried over sodium sulfate and concentrated to an oil, which on chromatographing on 250 g of silica gel (ethyl acetate-hexane; 30:70; v:v) gave 5.08 g of product, m.p. 79°-81° C.

Workup

  1. temperatureto reflux for 2 hours
  2. temperatureThe reaction was cooled
  3. filtrationthe solids filtered
  4. washwashed with ethyl acetate
  5. concentrationconcentrated in vacuo to an oil
  6. additionThe residue was treated with water (100 ml)
  7. extractionextracted with ethyl acetate (3×100 ml)
  8. washwashed with water until the pH of the washings
  9. washThe extracts were washed with a brine solution
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated to an oil, which on chromatographing on 250 g of silica gel (ethyl acetate-hexane; 30:70; v:v)

Sources & evidence

ORD record
ord-475f75382ee1408a8eef466d34eb7709
Source dataset
uspto-grants-1996_03
Patent number
US05498621

Reaction notes

Loading…