Sodium Carbonate → 4-Hydroxy-4-(5-methyl-thiazol-2-yl)-cyclohexanone

HRID 969582Notes

Reaction equation

HRID 969582 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2([OH:17])[CH2:16][CH2:15][C:10]3(OCC[O:11]3)[CH2:9][CH2:8]2)=[N:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[OH:17][C:7]1([C:5]2[S:6][C:2]([CH3:1])=[CH:3][N:4]=2)[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 590174448-(5-Methyl-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 590174344-Hydroxy-4-(5-methyl-thiazol-2-yl)-cyclohexanoneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-(5-methyl-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (1.0 g, 4.14 mmol) in 20 mL of THF/3 N HCl (1:1) was stirred for 1 h at 50° C. After cooling to room temperature, the mixture 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 0.82 g (99%) of the desired product. MS (M+H)+=212.2.

Workup

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

Sources & evidence

ORD record
ord-30025fdf142c419c970ac8a470e80207
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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