HCID 58542057, compound → HCID 58541981, compound

HRID 1966714Notes

Reaction equation

HRID 1966714 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][OH:16])[O:6][N:5]=1)([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH:1]([C:4]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]=[O:16])[O:6][N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58542057HCID 58542057, compound

Product 1

HCID 58541981HCID 58541981, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(3-isopropyl-1,2,4-oxadiazol-5-yl)-phenyl]methanol (373 mg, 1.71 mmol) in CH2Cl2 (5.0 mL) is added MnO2 (300 mg, 3.45 mmol). The reaction mixture is stirred at room temperature for 48 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 30% EtOAc in heptanes as the eluent to afford 2-(3-isopropyl-1,2,4-oxadiazol-5-yl)-benzaldehyde (139 mg, 37%).

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 30% EtOAc in heptanes as the eluent

Sources & evidence

ORD record
ord-8ea8591ca03743d2a4cd34f4d01204a7
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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