(4-(5-Ethyl-1,3,4-oxadiazol-2-yl)phenyl)methanol → HCID 58432034, compound

HRID 2359178Notes

Reaction equation

HRID 2359178 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)=[N:5][N:4]=1)[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=2)=[N:5][N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 58432072(4-(5-Ethyl-1,3,4-oxadiazol-2-yl)phenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 58432034HCID 58432034, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)methanol (1.8 g, 8.8 mmol) in CH2Cl2 (50 mL) was added molecular sieves (1.5 g, 4 Å) and the mixture was cooled to 0° C. Pyridinium chlorochromate (2.27 g, 10.5 mmol) was added in portions to the reaction mixture then it was warmed to room temperature. After stirring for 2 hrs, the mixture was filtered through Celite and rinsed with additional CH2Cl2. The filtrate was concentrated in vacuo. Purification by chromatography (EtOAc-hexanes) provided 4-(5-ethyl-1,3,4-oxadiazol-2-yl)benzaldehyde as an off-white solid (1.3 g, 70%).

Workup

  1. temperatureit was warmed to room temperature
  2. filtrationthe mixture was filtered through Celite
  3. washrinsed with additional CH2Cl2
  4. concentrationThe filtrate was concentrated in vacuo
  5. customPurification by chromatography (EtOAc-hexanes)

Sources & evidence

ORD record
ord-2eb9e54aa14e4eaebd65c5ced0fa3d99
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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