Hydrochloric Acid → 4-Hydroxy-4-(thiazol-5-yl)cyclohexanone

HRID 2096194Notes

Reaction equation

HRID 2096194 reaction equation
[S:1]1[C:5]([C:6]2([OH:16])[CH2:15][CH2:14][C:9]3(OCC[O:10]3)[CH2:8][CH2:7]2)=[CH:4][N:3]=[CH:2]1.Cl.C([O-])(O)=O.[Na+]>CC(C)=O>[OH:16][C:6]1([C:5]2[S:1][CH:2]=[N:3][CH:4]=2)[CH2:15][CH2:14][C:9](=[O:10])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 590174418-Hydroxy-8-(5-thiazolyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 590174394-Hydroxy-4-(thiazol-5-yl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8-Thiazol-5-yl-1,4-dioxa-spiro[4.5]decan-8-ol (4.35 g, 18.0 mmol) as prepared in the previous step was treated with 1N HCl (˜10 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 then 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 then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-e5c8ad2252924d178c8a033295e69a6f
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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