Potassium Carbonate → HCID 66926125, compound
Reaction equation
CO[C:3](=[O:22])[CH2:4][CH2:5][C:6](=[O:21])[CH2:7][N:8]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:9]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:10]2[CH:11]=[C:12]([CH3:13])[N:8]([CH:7]3[C:3](=[O:22])[CH2:4][CH2:5][C:6]3=[O:21])[N:9]=2)=[CH:19][CH:18]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
5-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl]-4-oxo-pentanoic acid methyl ester (1.7 g, 5.5 mmol) was dissolved in dimethylformamide (16 ml) and anhydrous potassium carbonate (3 g, 22 mmol) added. The mixture was then heated to 200° C. for 10 mins in the microwave (using “normal” absorbtion). The reaction was reduced in vacuo, and partitioned between 2 M hydrochloric acid (50 ml) and dichloromethane (100 ml). The layers were separated, and the aqueous layer saturated with sodium chloride and extracted with dichloromethane (100 ml). The organics were combined, dried over magnesium sulfate and the solvent removed in vacuo. The reaction was then purified by column chromatography (using DCM:EtOAc:AcOH (9:1:0.01%) to (3:7:0.01%)) to give 2-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl]-cyclopentane-1,3-dione (0.8 g).
Workup
- custompartitioned between 2 M hydrochloric acid (50 ml) and dichloromethane (100 ml)
- customThe layers were separated
- extractionthe aqueous layer saturated with sodium chloride and extracted with dichloromethane (100 ml)
- dry with materialdried over magnesium sulfate
- customthe solvent removed in vacuo
- customThe reaction was then purified by column chromatography (using DCM:EtOAc:AcOH (9:1:0.01%) to (3:7:0.01%))
Sources & evidence
- ORD record
- ord-4a86dc2873484c7d82676d23f4c2f2ae
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051300B2
Reaction notes
Loading…