Pyrazole → 1-(1H-pyrazol-1-yl)propan-2-one

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Cl[CH2:7][C:8](=[O:10])[CH3:9]>>[N:1]1([CH2:7][C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

Reactant 2

HCID 1048Pyrazole

HCID 6571Chloroacetone

Product 1

HCID 51550031-(1H-pyrazol-1-yl)propan-2-oneYield 37.6%

Conditions

Temperature: 90 °C

Procedure

1H-pyrazole (1.0 g, 15 mmol) was dissolved in chloroacetone (3.0 g, 32 mmol) and heated at 90° C. for 10 hr. Purification by silica gel column, elution with 1:1 hexanes:DCM afforded the title compound (700 mg): 1H NMR (400 MHz DMSO) delta 2.05 (s, 3H), 5.09 (s, 2H), 6.29 (t, J=2.0 Hz, 1H), 7.47 (dd, J=0.4, 1.6 Hz, 1H), 7.67 (dd, J=0.4, 2.0 Hz, 1H).

Workup

customPurification
washby silica gel column, elution with 1:1 hexanes

Sources & evidence

ORD record: ord-7c5d9c02003746089149facbdf12c4f8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901313B2

Reaction notes

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