Diethyl Ether → 2,6-Dichloropyridine-3-carbaldehyde

HRID 252133Notes

Reaction equation

HRID 252133 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.[Cr](Cl)([O-])(=O)=O.C(OCC)C>ClCCl>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12259932(2,6-Dichloropyridin-3-yl)methanolHCID 178479088HCID 178479088, compound

Product 1

HCID 122593832,6-Dichloropyridine-3-carbaldehydeYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (2,6-dichloropyridin-3-yl)-methanol (876 mg, 4.92 mmol) in dichloromethane (20 mL). Add pyridium chlorochromate (2.12 g, 9.84 mmol). Stir for 2 hours. Add diethyl ether and stir for 20 minutes. Filter the mixture through a pad of Celite® and silica gel and concentrate to give 2,6-dichloropyridine-3-carbaldehyde (575 mg, 66%): 1H NMR (400 MHz, CDCl3) δ 10.39 (s, 1H), 8.18 (d, 1H, J=8.0 Hz), 7.43 (d, 1H, J=8.0 Hz).

Workup

  1. filtrationFilter the mixture through a pad of Celite® and silica gel
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-a9c7d46797ed425eb9fd0453904b35e1
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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