(4-(Pyridin-2-yloxymethyl)-phenyl)-methanol → 4-((Pyridin-2-yloxy)methyl)benzaldehyde

HRID 557260Notes

Reaction equation

HRID 557260 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 59255473(4-(Pyridin-2-yloxymethyl)-phenyl)-methanol

Product 1

HCID 592551184-((Pyridin-2-yloxy)methyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4-(pyridin-2-yloxymethyl)-phenyl)methanol described in Preparation Example 1-3-1 (1.9 g, 8.6 mmol) and methylene chloride (30 mL) was added manganese dioxide (15 g, 17 mmol) at room temperature, which was stirred overnight at this temperature. The reaction mixture was filtered through a celite bed, and the solvent thereof was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:4) to obtain the title compound (770 mg).

Workup

  1. filtrationThe reaction mixture was filtered through a celite bed
  2. customthe solvent thereof was evaporated under a reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:4)

Sources & evidence

ORD record
ord-643ba2afb7614979a979497b77b99a84
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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