[4-(1,3-Oxazol-5-yl)phenyl]methanol → 4-(5-Oxazolyl)benzaldehyde

HRID 910232Notes

Reaction equation

HRID 910232 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[O:12]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=2)=[CH:15][N:14]=[CH:13]1>ClCCl>[O:12]1[C:16]([C:17]2[CH:18]=[CH:19][C:20]([CH:23]=[O:24])=[CH:21][CH:22]=2)=[CH:15][N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 45588265[4-(1,3-Oxazol-5-yl)phenyl]methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 105833464-(5-Oxazolyl)benzaldehydeYield 41.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (517 mg) and Celite (3 g) were suspended in dichloromethane (20 mL), and a solution of [4-(1,3-oxazol-5-yl)phenyl]methanol (280 mg) in dichloromethane (5 mL) was added to the suspension, followed by stirring at room temperature overnight. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified through flash column chromatography (n-hexane:ethyl acetate=2:1), followed by concentration, to thereby yield the title compound (115 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified through flash column chromatography (n-hexane:ethyl acetate=2:1)
  4. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-0a89fd77aa54430c9c948d8cf302d00c
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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