2-Fluoroethanol → 1-[6-(2-Fluoroethoxy)-3-pyridinyl]ethanone

HRID 633754Notes

Reaction equation

HRID 633754 reaction equation
[F:1][CH2:2][CH2:3][OH:4].[H-].[Na+].Cl[C:8]1[N:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=1>CN(C=O)C>[F:1][CH2:2][CH2:3][O:4][C:8]1[N:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 97372-FluoroethanolHCID 24758Sodium hydrideHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 586290251-[6-(2-Fluoroethoxy)-3-pyridinyl]ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

530 μl (8.68 mmol) of 2-fluoroethanol are added to a suspension of 347.05 mg (8.68 mmol) of sodium hydride in 10 mL of DMF. The reaction mixture is placed under magnetic stirring at room temperature for 15 minutes. A solution of 500 mg (2.89 mmol) of 1-(6-chloropyrid-3-yl)ethanone in 3 mL of DMF is added dropwise to the reaction medium. The reaction is stirred at room temperature overnight. The reaction medium is evaporated to dryness. The crude product is taken up in water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. After purification by chromatography on silica gel (eluent A/B: heptane/EtOAc, gradient A/B: t 0 min 0% B, t 5 min 10% B, t 30 min 30% B), 362 mg of 1-[6-(2-fluoroethoxy)pyrid-3-yl]ethanone were obtained, corresponding to the following characteristics:

Workup

  1. stirringThe reaction is stirred at room temperature overnight
  2. customThe reaction medium is evaporated to dryness
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customevaporated to dryness
  6. customAfter purification by chromatography on silica gel (eluent A/B: heptane/EtOAc, gradient A/B: t 0 min 0% B, t 5 min 10% B, t 30 min 30% B), 362 mg of 1-[6-(2-fluoroethoxy)pyrid-3-yl]ethanone
  7. customwere obtained, corresponding to the following characteristics

Sources & evidence

ORD record
ord-71e39949dcf742e9af2955b1cf04ce8b
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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