3-(2-Fluoropyridin-3-yl)cyclohex-2-enone → (Rac)-3-(2-fluoropyridin-3-yl)-1-methylcyclohex-2-enol

HRID 473658Notes

Reaction equation

HRID 473658 reaction equation
[CH3:1][Mg]Cl.[F:4][C:5]1[C:10]([C:11]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH:12]=2)=[CH:9][CH:8]=[CH:7][N:6]=1>C1COCC1>[F:4][C:5]1[C:10]([C:11]2[CH2:16][CH2:15][CH2:14][C:13]([CH3:1])([OH:17])[CH:12]=2)=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 593269873-(2-Fluoropyridin-3-yl)cyclohex-2-enoneHCID 178418332HCID 178418332, compound

Product 1

HCID 67416977(Rac)-3-(2-fluoropyridin-3-yl)-1-methylcyclohex-2-enol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 3.0 M solution of methylmagnesium chloride in tetrahydrofuran (4.88 mL, 14.64 mmol) was added slowly to a solution of 3-(2-fluoropyridin-3-yl)cyclohex-2-enone (2.00 g, 10.46 mmol) in THF (20 ml) at −78° C. After completion of the addition the reaction mixture was stirred overnight while it gradually warmed up to RT. It was cooled in an ice water bath and distilled water (5 ml) was added slowly. The mixture was concentrated under reduced pressure, saturated aqueous sodium bicarbonate (200 ml) was added, and it was extracted EtOAc (3×100 ml). The combined organic layers were washed by brine and dried over sodium sulfate. Filtration and concentration under reduced pressure gave (rac)-3-(2-fluoropyridin-3-yl)-1-methylcyclohex-2-enol as a light yellow liquid. MS (ESI, pos. ion) m/z: 208.0 (M+1).

Workup

  1. additionAfter completion of the addition the reaction mixture
  2. temperatureIt was cooled in an ice water bath
  3. distillationdistilled water (5 ml)
  4. additionwas added slowly
  5. concentrationThe mixture was concentrated under reduced pressure, saturated aqueous sodium bicarbonate (200 ml)
  6. additionwas added
  7. extractionit was extracted EtOAc (3×100 ml)
  8. washThe combined organic layers were washed by brine
  9. dry with materialdried over sodium sulfate
  10. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-c4beffa3c4fd433c9fce2e3a01146599
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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