4-Pyridinepropanol → 3-(Pyridin-4-yl)propanal

HRID 1166080Notes

Reaction equation

HRID 1166080 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][OH:10])=[CH:3][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][C:4]([CH2:7][CH2:8][CH:9]=[O:10])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 729234-PyridinepropanolHCID 159087Triacetoxyperiodinane

Product 1

HCID 226308883-(Pyridin-4-yl)propanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-pyridinepropanol (0.60 mL, 4.65 mmol) was added to a solution of the Dess-Martin reagent (2.37 g, 5.58 mol) in dichloromethane (30 mL). After 60 min at RT, the solution was quenched with 10% aq. Na2S2O3, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded the title compound. MS 136 (M+H)+.

Workup

  1. customthe solution was quenched with 10% aq. Na2S2O3
  2. washwashed with sat. aq. NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-08576c79e3844788b5f92a6292a7dc67
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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