(5,6-Dichloropyridin-3-yl)methanol → 5,6-Dichloropyridine-3-carbaldehyde

HRID 730865Notes

Reaction equation

HRID 730865 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[N:6][C:7]=1[Cl:8]>O=[Mn]=O.C(Cl)Cl.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 115356545,6-Dichloropyridine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 21226440Methylenechloride HexaneSolvent

Procedure

A mixture of (5,6-dichloro-pyridin-3-yl)-methanol (1.78 g, 10 mmol, TCI-US) and MnO2 (17.39 g, 200 mmol, Aldrich) in 1:1 CH2Cl2/hexane (10 ml) was stirred at room temperature for 1 h. The catalyst was filtered and washed with 50% EtOAc/hexane. The filtrate was evaporated and the residue dried in vacuo to give the title compound product, which was used in the next step without additional purification. MS (ESI, pos. ion) m/z: 176 (M+1).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with 50% EtOAc/hexane
  3. customThe filtrate was evaporated
  4. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-e8e6b4a92cf84553a65abfbc4f4fd6b5
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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