Oxyselenide → 3-(Difluoromethyl)-2-pyridinecarboxaldehyde

HRID 1170907Notes

Reaction equation

HRID 1170907 reaction equation
[F:1][CH:2]([F:10])[C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[Se]=[O:12]>O1CCOCC1>[F:1][CH:2]([F:10])[C:3]1[C:4]([CH:9]=[O:12])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 167175OxyselenideHCID 18629366HCID 18629366, compound

Product 1

HCID 595538943-(Difluoromethyl)-2-pyridinecarboxaldehydeYield 9.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(difluoromethyl)-2-methylpyridine (110 mg, 0.768 mmol) and selenium oxide (102 mg, 0.922 mmol) in 1,4-dioxane (3 mL) was warmed at reflux for twelve hours. The reaction mixture was then concentrated and purified with flash chromatography (12+S Biotage, heptane/ethyl acetate=1:0 to 1:1), to give 3-(difluoromethyl)picolinaldehyde as an oil (11 mg). 1H NMR (400 MHz, CDCl3) δ 10.1 (s, 1H), 8.90 (d, 1H), 8.22 (d, 1H), 7.64 (m, 1H), 7.59 (t, 1H).

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for twelve hours
  3. concentrationThe reaction mixture was then concentrated
  4. custompurified with flash chromatography (12+S Biotage, heptane/ethyl acetate=1:0 to 1:1)

Sources & evidence

ORD record
ord-1221a020123b4d84a0a4abad76e40760
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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