3-Pyridinemethanol, 5-chloro-6-(2,2,2-trifluoroethoxy)- → 5-Chloro-6-(2,2,2-trifluoroethoxy)nicotinaldehyde

HRID 57454Notes

Reaction equation

HRID 57454 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][OH:15])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11]>CCOC(C)=O.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]([F:12])([F:13])[F:11])=[N:6][CH:5]=[C:4]([CH:3]=1)[CH:14]=[O:15]

Participants

4

Reactant 1

HCID 612563313-Pyridinemethanol, 5-chloro-6-(2,2,2-trifluoroethoxy)-

Product 1

HCID 867302085-Chloro-6-(2,2,2-trifluoroethoxy)nicotinaldehydeYield 85.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (5-chloro-6-(2,2,2-trifluoroethoxyl)pyridin-3-yl)methanol (4.00 g, 16.56 mmol) in EtOAc (15 mL) was added manganese(IV) oxide (16.93 g, 166 mmol). The reaction was heated with microwave at 120° C. for 30 minutes. The mixture was then filtered through a pad of celite, and rinsed with EtOAc. The filtrated was concentrated to give crude product (3.38 g).

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. washrinsed with EtOAc
  3. concentrationThe filtrated was concentrated

Sources & evidence

ORD record
ord-431ab923f0694d56b75b8f4420f55947
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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