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

HRID 2046948Notes

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

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole (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

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

Sources & evidence

ORD record: ord-5473d9e9d6b94b53a58f7dbf5b34cd0a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592448B2

Reaction notes

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