Ammonium Chloride → 1-(6-(Trifluoromethyl)pyridin-3-yl)ethanol

HRID 2062122Notes

Reaction equation

HRID 2062122 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][CH:4]=1.[CH3:13][Mg]Cl.[Cl-].[NH4+]>C1COCC1>[F:12][C:2]([F:11])([F:1])[C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:10])[CH3:13])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 497603801-(6-(Trifluoromethyl)pyridin-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.0 g 6-trifluoromethyl-pyridine-3-carboxaldehyde in 20 mL of dry THF under inert atmosphere at −78° C. was added dropwise 6 ml of MeMgCl (3 M in THF). This mixture was allowed to warm up to room temperature slowly. Aqueous ammonium chloride was added to reaction mixture. The whole was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulphate. Purification by flash chromatography (silica, haptane/ethyl acetate) provided 0.85 g of 1-(6-trifluoromethyl-pyridin-3-yl)-ethanol.

Workup

  1. extractionThe whole was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulphate
  4. customPurification by flash chromatography (silica, haptane/ethyl acetate)

Sources & evidence

ORD record
ord-c4fc367516d243c09f0dd4f636226558
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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