HCID 59255222, compound → HCID 59255438, compound

HRID 78141Notes

Reaction equation

HRID 78141 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[O:15])[CH:11]=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59255222HCID 59255222, compound

Product 1

HCID 59255438HCID 59255438, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (20 mL) solution of (5-phenoxy-pyridin-3-yl)-methanol (756 mg, 3.76 mmol) described in Manufacturing Example 145-1-2 was added manganese(IV) dioxide (3.27 g, 37.6 mmol), which was stirred for 2 hours at room temperature. The insolubles were removed by filtrating through a Celite pad, after which the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane: ethyl acetate=2:1 to 1:1) to obtain the title compound (607 mg, 81%).

Workup

  1. customThe insolubles were removed
  2. filtrationby filtrating through a Celite pad
  3. concentrationafter which the filtrate was concentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane: ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record
ord-d9418dfa85814c5da5f154a90c182e92
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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