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

HRID 1173248Notes

Reaction equation

HRID 1173248 reaction equation
[CH:1]([C:4]1[S:5][C:6]([C:9]2([OH:19])[CH2:18][CH2:17][C:12]3(OCC[O:13]3)[CH2:11][CH2:10]2)=[CH:7][N:8]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[OH:19][C:9]1([C:6]2[S:5][C:4]([CH:1]([CH3:3])[CH3:2])=[N:8][CH:7]=2)[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 595561458-(2-Isopropyl-1,3-thiazol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 595561884-Hydroxy-4-(2-isopropylthiazol-5-yl)cyclohexanoneYield 107.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-(2-isopropyl-1,3-thiazol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol (0.714 g, 2.52 mmol) in 15 mL of THF/1N HCl (1:1) was stirred overnight at 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 0.65 g of 4-hydroxy -4-(2-isopropyl-1,3-thiazol-5-yl)cyclohexanone in 98% yield. MS (EI) calcd: (M+H)+=240.1; found: 240.0.

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-f89333cd274f43cc847241692d4468ef
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

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