3-Pyridinepropanol → 3-(Pyridin-3-yl)propanal

HRID 1186391

Reaction equation

HRID 1186391 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=[O:10])[CH:2]=1

Participants

4

Reactant 2

HCID 178613-PyridinepropanolHCID 159087Triacetoxyperiodinane

Product 1

HCID 111054123-(Pyridin-3-yl)propanalYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Pyridinepropanol (300 mg, 2.2 mmol) was dissolved in dichloromethane (5 mL). To this, the Dess-Martin reagent (1.0 g) was added with cooling in an ice bath and the mixture was stirred at the same temperature for 2 hours and successively at room temperature for 3 hours. The solvent in the reaction mixture was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 10/1) to give 3-(pyridin-3-yl)propanal (180 mg, yield: 61%).

Workup

  1. temperaturewith cooling in an ice bath
  2. customThe solvent in the reaction mixture was evaporated off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 10/1)

Sources & evidence

ORD record
ord-d0c2e372d0714bb590a9d46cd7f14c27
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Linked notes

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