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

HRID 410474Notes

Reaction equation

HRID 410474 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-c730726318244cf785bf4f91c9056fb2
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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