Hydrochloric Acid → 4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)cyclohexanone

HRID 2047200Notes

Reaction equation

HRID 2047200 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=3)[CH2:7][CH2:6]2)[O:4]CC1.O.Cl>CCO.O1CCOCC1>[CH3:21][Si:20]([CH3:23])([CH3:22])[CH2:19][CH2:18][O:17][CH2:16][N:14]1[CH:15]=[C:11]([CH:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)[CH:12]=[N:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 674943514-(1,4-dioxaspiro[4.5]decan-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

Product 1

HCID 667336444-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)cyclohexanoneYield 98.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(1,4-dioxaspiro[4.5]decan-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (487 μmol, 165 mg) was dissolved in EtOH (10 mL) in a 20 mL scintillation vial. To this solution was added H2O (3 mL) followed by 4N HCl in 1,4-dioxane. The resulting reaction mixture was stirred at room temperature for 60 hours. At this point, the reaction was quenched with saturated NaHCO3(aq) and extracted with DCM (×3). The combined organics were dried over Na2SO4 to yield 4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)cyclohexanone (141 mg, 480 μmol, 98% yield) as white solid.

Workup

  1. customThe resulting reaction mixture
  2. customAt this point, the reaction was quenched with saturated NaHCO3(aq)
  3. extractionextracted with DCM (×3)
  4. dry with materialThe combined organics were dried over Na2SO4

Sources & evidence

ORD record
ord-037cc26e09ef460a9acaccefa32cd08a
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

Loading…