HCID 58542045, compound → HCID 58542031, compound

HRID 1966776Notes

Reaction equation

HRID 1966776 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[N:11]([CH3:15])[N:12]=[CH:13][N:14]=2)=[C:6]([CH2:8][OH:9])[CH:7]=1>C(Cl)Cl.O=[Mn]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[N:11]([CH3:15])[N:12]=[CH:13][N:14]=2)=[C:6]([CH:7]=1)[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 58542045HCID 58542045, compound

Product 1

HCID 58542031HCID 58542031, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-fluoro-2-(2-methyl-2H-1,2,4-triazol-3-yl)-phenyl]-methanol plus regiosiomer (600 mg, 2.90 mmol) in CH2Cl2 (20.0 mL) is added MnO2 (750 mg, 8.63 mmol). The reaction mixture is stirred at room temperature for 72 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 6% MeOH in CH2Cl2 as the eluent to afford 5-fluoro-2-(2-methyl-2H-1,2,4-triazol-3-yl)-benzaldehyde plus regioisomer (475 mg, 80%).

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 6% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-8c25cee032094ac798ea25b1332e089c
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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