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

HRID 8977Notes

Reaction equation

HRID 8977 reaction equation
[O:1]1[C:5]([C:6]2[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1>C(Cl)Cl.CO.C(Cl)Cl.O=[Mn]=O>[O:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH:10]=[O:11])=[CH:12][CH:13]=2)=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 1

HCID 45588265[4-(1,3-Oxazol-5-yl)phenyl]methanol

Product 1

HCID 105833464-(5-Oxazolyl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of the 4-(oxazol-5-yl)benzyl alcohol (prepared as described by Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. J. Med. Chem. 1998, 41, 2390–2410) (0.23 g, 1.31 mmol) in CH2Cl2/MeOH (20:1, 10.5 mL) was added activated MnO2 (1.01 g, 11.6 mmol) and the mixture stirred at room temperature overnight. The reaction was then diluted with CH2Cl2 (10 mL) and filtered through Celite®, washing with CHCl3. The filtrate was concentrated to give the crude aldehyde as a beige solid (0.164 g) which used without further purification in the next reaction. 1H NMR (CDCl3) δ 7.52 (s, 1H), 7.82 (d, 2H, J=9 Hz), 7.95 (d, 2H, J=9 Hz), 7.99 (s, 1H), 10.02 (s, 1H).

Workup

  1. filtrationfiltered through Celite®
  2. washwashing with CHCl3
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-58d9d2451cc241dba47c7b8c690cd786
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Reaction notes

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