Hydrochloric Acid → 4-(3-Hydroxy-pyridin-2-yl)-cyclohexanone

HRID 1896801Notes

Reaction equation

HRID 1896801 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl.C([O-])(O)=O.[Na+]>C(#N)C>[OH:17][C:16]1[C:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 585628682-(1,4-Dioxa-spiro[4.5]dec-8-yl)-pyridin-3-ol

Product 1

HCID 585626334-(3-Hydroxy-pyridin-2-yl)-cyclohexanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(1,4-dioxa-spiro[4.5]dec-8-yl)-pyridin-3-ol (1.30 g, 5.52 mmol) as prepared in the previous step was treated with 1N HCl (˜16 mL) in acetonitrile (100 mL) at room temperature for 4 hours. The reaction was neutralized with saturated NaHCO3 solution and the solvent was removed. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow solid, which was purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a pale yellow solid.

Workup

  1. customthe solvent was removed
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow solid, which
  8. customwas purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-9e70e99c53bb4e949b6a71b6006b4934
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

Loading…