Sodium Carbonate → 4-Hydroxy-4-thiazol-2-yl-cyclohexanone

HRID 1809903Notes

Reaction equation

HRID 1809903 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1([OH:16])[CH2:15][CH2:14][C:9]2(OCC[O:10]2)[CH2:8][CH2:7]1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[OH:16][C:6]1([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH2:15][CH2:14][C:9](=[O:10])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 578033298-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 590174374-Hydroxy-4-thiazol-2-yl-cyclohexanoneYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-(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 (3×). The combined organic layers were washed with saturated NaCl solution, dried (MgSO4), and concentrated to give 0.82 g of 4-hydroxy-4-(1,3-thiazol-2-yl)cyclohexanone in 99% yield. MS (EI) calcd: (M+H)+=198.1. Found: 198.2.

Workup

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

Sources & evidence

ORD record
ord-0451bc621ea9407c94462287ff1e393f
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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