Sodium Carbonate → 4-(Thiazol-2-yl)cyclohexan-1-one

HRID 1025754Notes

Reaction equation

HRID 1025754 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)[CH2:7][CH2:6]2)[O:4]CC1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[S:12]1[CH:13]=[CH:14][N:15]=[C:11]1[CH:8]1[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 595560502-(1,4-Dioxa-spiro[4.5]dec-8-yl)-thiazole

Product 1

HCID 595561194-(Thiazol-2-yl)cyclohexan-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(1,4-dioxaspiro[4.5]dec-8-yl)-1,3-thiazole (0.21 g, 0.93 mmol) in 10 mL of THF/3NHCl (1:1) was stirred for 2 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 0.16 g of 4-(1,3-thiazol-2-yl)cyclohexanone in 95% yield. MS (EI) calcd: (M+H)+=182.1; found: 181.9.

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-d0d9d2c8930945268eef22a2858999a9
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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