HCID 58541954, compound → HCID 58541980, compound

HRID 1966717Notes

Reaction equation

HRID 1966717 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[O:14][N:13]=[C:12]([CH3:15])[N:11]=2)=[C:6]([CH2:8][OH:9])[CH:7]=1>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[O:14][N:13]=[C:12]([CH3:15])[N:11]=2)=[C:6]([CH:7]=1)[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 58541954HCID 58541954, compound

Product 1

HCID 58541980HCID 58541980, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)-phenyl]-methanol (78 mg, 0.35 mmol) in CH2Cl2 (5.0 mL) is added MnO2 (125 mg, 1.22 mmol). The reaction mixture is stirred at room temperature for 16 hours and is filtered through diatomaceous earth. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 40% EtOAc in heptanes as the eluent to afford 5-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)-benzaldehyde (27 mg, 35%).

Workup

  1. filtrationis filtered through diatomaceous earth
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue is purified by silica gel flash column chromatography with 40% EtOAc in heptanes as the eluent

Sources & evidence

ORD record
ord-8f37b578cc064665a6db3f1537d9a21c
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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