Dimethylformamide → 3-Pyridinecarboxaldehyde, 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-

HRID 2199842Notes

Reaction equation

HRID 2199842 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[N:6][CH:7]=1.C([Mg]Cl)(C)C.CN([CH:26]=[O:27])C>C1COCC1>[F:10][C:9]([F:12])([F:11])[C:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([CH:3]=1)[CH:26]=[O:27])([OH:17])[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 177589312-(5-Bromopyridin-3-yl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 178418918HCID 178418918, compound

Product 1

HCID 177581373-Pyridinecarboxaldehyde, 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 258 (0.347 g, 1.07 mmol) in dry THF, cooled to 0° C., was added isopropyl magnesium chloride (1.2 mL, 2.4 mmol) drop wise and stirred for 10 min followed by the addition of DMF (0.015 ml, 1.94 mmol) to the reaction and stirred for additional 2 h. After completion of the reaction, it was quenched with saturated ammonium chloride solution. The organic layer was separated and aqueous phase was extracted again with diethyl ether, the combined organic layer was dried over sodium sulphate and concentrated to get the crude compound 5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)nicotinaldehyde 259 used directly to proceed for the next step.

Workup

  1. stirringstirred for additional 2 h
  2. customAfter completion of the reaction, it
  3. customwas quenched with saturated ammonium chloride solution
  4. customThe organic layer was separated
  5. extractionaqueous phase was extracted again with diethyl ether
  6. dry with materialthe combined organic layer was dried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b3bced091fea4ed79278cb9199900d11
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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