Acetone → 4-(4-iodo-1H-pyrazol-1-yl)cyclohexanone

HRID 511338

Reaction equation

HRID 511338 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH:15]=[C:14]([I:16])[CH:13]=[N:12]3)[CH2:7][CH2:6]2)[O:4]CC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CC(C)=O>O>[I:16][C:14]1[CH:13]=[N:12][N:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH:15]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 595411251-(1,4-Dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole2×

Product 1

HCID 595411654-(4-iodo-1H-pyrazol-1-yl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole (Compound 137F, 3.0 g, 8.9 mmol), pyridinium p-toluenesulfonate (4.5 g, 17.9 mmol), acetone (100 mL) and H2O (100 mL) was heated at 60° C. overnight. Work-up: Solvent was evaporated and the residue was extracted with EtOAc (3×60 mL). The combined extracts were washed with water (3×50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound as white solid. It was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ=2.23-2.63 (m, 8 H), 4.57-4.64 (m, 1 H), 7.51 (s, 1 H), 7.54 (s, 1 H). MS (ES+): m/z=291.09 (100). HPLC: tR=2.79 min (polar—5 min, ZQ3).

Workup

  1. customSolvent was evaporated
  2. extractionthe residue was extracted with EtOAc (3×60 mL)
  3. washThe combined extracts were washed with water (3×50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80f03c31f257450fb7fdd2f7858debbb
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Linked notes

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