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

HRID 511338

Reaktionsgleichung

Reaktionsgleichung von HRID 511338
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

Komponenten

5

Edukt 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×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-80f03c31f257450fb7fdd2f7858debbb
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096624B2

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