Hydrochloric Acid → 4-Hydroxy-4-(6-methoxypyridin-3-YL)cyclohexanone

HRID 2388296Notes

Reaction equation

HRID 2388296 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2([OH:19])[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl.C([O-])(O)=O.[Na+]>CC(C)=O>[OH:19][C:9]1([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 595560668-Hydroxy-8-(6-methoxy-3-pyridyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 529879954-Hydroxy-4-(6-methoxypyridin-3-YL)cyclohexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8-(6-Methoxy-pyridin-3-yl)-1,4-dioxa-spiro[4.5]decan-8-ol (4.00 g, 15.7 mmol) as prepared in the previous step was treated with 1N HCl (˜16 mL) in acetone (20 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-d8bb489ba6404db0923602e9d2abceef
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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