Hydrochloric Acid → 4-(2-Fluoropyridin-3-yl)cyclohexanone

HRID 410242Notes

Reaction equation

HRID 410242 reaction equation
[F:1][C:2]1[C:7]([CH:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl>CC(C)=O>[F:1][C:2]1[C:7]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 593272352-Fluoro-3-(1,4-dioxaspiro[4.5]decan-8-yl)pyridine

Product 1

HCID 576067214-(2-Fluoropyridin-3-yl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-fluoro-3-(1,4-dioxaspiro[4.5]decan-8-yl)pyridine (7.88 g, 33.2 mmol) in acetone (350 mL) was added aqueous hydrochloric acid (39.9 mL, 39.9 mmol, 1N). The mixture was heated to 45° C. for 5 h, then cooled to room temperature. Most of the organic solvent was removed in vacuo and ethyl acetate (200 mL) was added. The resulting solution was washed with saturated aqueous sodium bicarbonate (2×), water (1×), saturated aqueous sodium chloride (1×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 4-(2-fluoropyridin-3-yl)cyclohexanone. MS (ESI, pos. ion) m/z: 194.1 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. customMost of the organic solvent was removed in vacuo and ethyl acetate (200 mL)
  3. additionwas added
  4. washThe resulting solution was washed with saturated aqueous sodium bicarbonate (2×), water (1×), saturated aqueous sodium chloride (1×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65a63b7561354f1d920598e1cab82a8e
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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