4-(5-(Trifluoromethyl)pyridin-2-yl)benzaldehyde → 1-[4-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-pentan-1-ol

HRID 1669300Notes

Reaction equation

HRID 1669300 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[CH2:19]([Mg]Br)[CH2:20][CH2:21][CH3:22]>C1COCC1>[F:18][C:2]([F:17])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]([OH:14])[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 27633594-(5-(Trifluoromethyl)pyridin-2-yl)benzaldehydeHCID 178418682HCID 178418682, compound

Product 1

HCID 673422541-[4-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-pentan-1-olYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-trifluoromethyl-pyridin-2-yl)-benzaldehyde (1.0 g, 3.98 mmol) in andhydrous tetrahydrifuran (THF) (25 mL) that had been cooled to 0° C. in an ice bath is added n-butyl magnesium bromide (8.0 mL, 16.0 mmol) dropwise with stirring under nitrogen. The mixture is allowed to warm slowly to room temperature. The reaction is monitored by HPLC, and upon complete consumption of the aldehyde, quenched with 1N HCl. The mixture is diluted with ethyl ether and water, then extracted. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The title compound is obtained after column chromatography (1.10 g or 3.20 mmol) at 80% yield.

Workup

  1. customupon complete consumption of the aldehyde
  2. customquenched with 1N HCl
  3. additionThe mixture is diluted with ethyl ether and water
  4. extractionextracted
  5. washThe organic layer is washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d34862f7ae145e693cf5479a557bc1d
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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