Diethyl Ether → 1-(6-Fluoropyridin-3-yl)ethan-1-one

HRID 339073Notes

Reaction equation

HRID 339073 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5](C#N)=[CH:4][N:3]=1.C[Mg]Br.C(=O)(O)[O-].[Na+].CC[O:20][CH2:21][CH3:22]>C1COCC1>[F:1][C:2]1[N:3]=[CH:4][C:5]([C:21](=[O:20])[CH3:22])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 157659642-Fluoropyridine-5-carbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 130903391-(6-Fluoropyridin-3-yl)ethan-1-oneYield 14.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-fluoronicotinonitrile (5.00 g, 41.0 mmol) in THF (50 mL) was added 1 N methylmagnesium bromide (16.4 mL, 49.1 mmol) in THF at 0° C. After addition, the mixture was warmed to ambient temperature and stirred at ambient temperature for 4 hours. Saturated sodium bicarbonate solution (50 mL) and ether (100 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give 1-(6-fluoropyridin-3-yl)ethanone (0.85 g, 14.9%) as solid.

Workup

  1. additionAfter addition
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7b9bfa6b3acb4225acadabaf78514a12
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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