Methanol → 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde

HRID 576081Notes

Reaction equation

HRID 576081 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.CON(C)[C:14]([C:16]1[CH:17]=[N:18][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:20][CH:21]=1)=[O:15].CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[F:27][C:24]([F:25])([F:26])[CH2:23][O:22][C:19]1[N:18]=[CH:17][C:16]([CH:14]=[O:15])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 86707284N-methoxy-N-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide

Product 1

HCID 216984996-(2,2,2-Trifluoroethoxy)nicotinaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diisobutylaluminum hydride (toluene solution, 1.01 mol/L, 1.95 mL, 1.97 mmol) was added dropwise to a solution of N-methoxy-N-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide obtained (432 mg, 1.64 mmol) in toluene (11 mL) at −78° C. under a nitrogen atmosphere. The mixture was stirred at the same temperature for 1 hr. Methanol (5 mL) was added dropwise to the reaction mixture, the mixture was warmed to room temperature, and 50% aqueous Rochelle salt solution (10 mL) was added thereto, followed by stirring for 1.5 hr. The mixture was extracted with chloroform and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→7:3) to afford the title compound as a colorless solid (287 mg).

Workup

  1. stirringby stirring for 1.5 hr
  2. extractionThe mixture was extracted with chloroform
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→7:3)

Sources & evidence

ORD record
ord-3d89b99031da442290db81348a05890f
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

Loading…