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

HRID 2075554Notes

Reaction equation

HRID 2075554 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-28ece7bb32404a82a76a3037c5fdb871
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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