HCID 12181442, compound → 3-(3-Pyridinyl)-2-propynal

HRID 50574Notes

Reaction equation

HRID 50574 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][OH:10])[CH:2]=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH:9]=[O:10])[CH:2]=1

Participants

3

Reactant 1

HCID 12181442HCID 12181442, compound

Product 1

HCID 227351693-(3-Pyridinyl)-2-propynalYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(3-pyridinyl)-2-propynol (500 mg, 3.75 mmol) in CH2Cl2 (5 mL) was treated with activated manganous dioxide (3.3 g, 34.5 mmol) at 25° C. After 12 h, the reaction mixture was filtered through celite, washed with CH2Cl2 (2×50 mL), concentrated in vacuo. Purification by flash chromatography afforded the title compound (100 mg, 20%) as yellow brown oil. MS 133 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. washwashed with CH2Cl2 (2×50 mL)
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-aee94fb66d904832999dbb007280ff5f
Source dataset
uspto-grants-2004_03
Patent number
US06713455B2

Reaction notes

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