Hydrochloric Acid → 4-(5-Bromothiazol-2-yl)-4-hydroxycyclohexanone

HRID 1039966Notes

Reaction equation

HRID 1039966 reaction equation
[Br: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.Cl.CCOC(C)=O.O>C1COCC1>[Br:1][C:2]1[S:6][C:5]([C:7]2([OH:17])[CH2:8][CH2:9][C:10](=[O:11])[CH2:15][CH2:16]2)=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 672560328-(5-Bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 672574234-(5-Bromothiazol-2-yl)-4-hydroxycyclohexanoneYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 1 (3.0 g, 9.4 mmol) was dissolved in 30 mL of 1:1 THF:HCl (3N) and heated at 50° C. for 8 hours and the solution neutralized with solid KHCO3 and then EtOAc (100 mL) and water (20 mL) were added. The aqueous layer was then extracted with EtOAc (50 mL) and the combined organic layers were washed with brine (50 mL), evaporated to a slurry which was treated with hexanes (20 mL). Filtration and drying afforded 4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxycyclohexanone as a white solid (2.1 g, 7.7 mmol).

Workup

  1. extractionThe aqueous layer was then extracted with EtOAc (50 mL)
  2. washthe combined organic layers were washed with brine (50 mL)
  3. customevaporated to a slurry which
  4. additionwas treated with hexanes (20 mL)
  5. filtrationFiltration
  6. customdrying

Sources & evidence

ORD record
ord-78a352d8d84c42c68f2ff3aae01a756a
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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