[5-(3-Fluoro-benzyloxy)-pyridin-2-yl]-methanol → 5-(3-Fluoro-benzyloxy)-pyridine-2-carbaldehyde

HRID 433213Notes

Reaction equation

HRID 433213 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][OH:14])=[N:11][CH:12]=1>O=[Mn]=O.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]=[O:14])=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 11148991[5-(3-Fluoro-benzyloxy)-pyridin-2-yl]-methanol

Product 1

HCID 111722915-(3-Fluoro-benzyloxy)-pyridine-2-carbaldehydeYield 80%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of [5-(3-fluoro-benzyloxy)-pyridin-2-yl]-methanol (3.8 g, 16.3 mmol), MnO2 (12 g, 138 mmol) and chloroform (50 ml) was heated under reflux for 30 min. The dark solids were then removed by filtration over celite. The filtrate was evaporated and the residue purified by chromatography (SiO2, AcOEt-hexanes 1:1) to afford the title compound (3.0 g, 80%) as a light yellow oil with solidified on standing. MS: m/e=232.2 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. customThe dark solids were then removed by filtration over celite
  4. customThe filtrate was evaporated
  5. customthe residue purified by chromatography (SiO2, AcOEt-hexanes 1:1)

Sources & evidence

ORD record
ord-4b2002b963c943b5822fd958ffa05b7e
Source dataset
uspto-grants-2003_12
Patent number
US06667327B2

Reaction notes

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