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

HRID 512618Notes

Reaction equation

HRID 512618 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-e7e1937af91c491e84e0e1b109b46ab6
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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