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

HRID 1015993Notes

Reaction equation

HRID 1015993 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.[OH-].[Na+]>C1COCC1>[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 14798Sodium HydroxideHCID 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 8028TetrahydrofuranSolvent

Procedure

To a solution of the ketal of step D (11.5 g, 43.3 mmol) in THF (100 mL) was added 3N HCl (75 mL) and the solution stirred overnight at rt. The pH of the solution was adjusted to ˜11 by the addition of 3N NaOH solution. After removal of most of the THF by rotary evaporation, the aqueous was extracted with CH2Cl2 (3×). The combined extracts were dried (MgSO4), filtered, and concentrated to give the title compound as a yellow solid; yield 8.2 g, 37.1 mmol, 86%; 1H NMR (CDCl3) δ 8.26 (s, 1H), 7.75 (d, 1H), 6.73 (d, 1H), 3.91 (s, 3H), 2.91 (m, 2H), 2.78 (s, 1H), 2.32 (m, 2H), 2.21 (m, 4H); MS m/z=222.1.

Workup

  1. customAfter removal of most of the THF
  2. customby rotary evaporation
  3. extractionthe aqueous was extracted with CH2Cl2 (3×)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9e617c90581a461989dfda006e222b07
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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