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

HRID 969585Notes

Reaction equation

HRID 969585 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+].[Na+]>C1COCC1>[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 10340Sodium CarbonateHCID 590174418-Hydroxy-8-(5-thiazolyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 590174394-Hydroxy-4-(thiazol-5-yl)cyclohexanoneYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-(1,3-thiazol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol (0.95 g, 4.14 mmol) in THF (20 mL) was added an aqueous solution of 3 N HCl (10 mL). The mixture was stirred for 1 h at 50° C. After cooling to room temperature, the solution was treated with Na2CO3 to pH 8 and extracted with EtOAc three times. The combined organic layers were washed with saturated NaCl solution, dried (MgSO4), and concentrated to give 0.78 g (98%) of the desired product. MS (M+H)+=198.2.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layers were washed with saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4837684861564d86aca5fdf67029f940
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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