Reaction equation
[C:1](O)([CH3:4])([CH3:3])[CH3:2].[CH3:6][N:7]1[C:11]([CH3:12])=[CH:10][C:9](=[O:13])[N:8]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.B(F)(F)F.[OH-].[Na+]>ClC(Cl)C>[C:1]([C:10]1[C:9](=[O:13])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:7]([CH3:6])[C:11]=1[CH3:12])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution tert-butanol (800 μL) and 1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.150 g) in dichloroethane (1 mL) was added boron trifluoride diethyletherate (400 μL). The reaction was heated to 40° C. over seven days. The reaction mixture was then cooled and poured onto an ice/water mixture, was basified to pH 10 using sodium hydroxide solution and was extracted with EtOAc. The solution was acidified with AcOH to pH=4 and further extracted with EtOAc. The combined organic phases were washed with brine and dried over sodium sulfate. Filtration and evaporation of the volatiles in vacuo afforded a crude residue which was purified via flash column chromatography to afford 4-tert-butyl-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.025 mg) as a white solid. MS (ESI+): 245.4 [M+H]+).
Workup
- temperatureThe reaction mixture was then cooled
- extractionwas extracted with EtOAc
- extractionfurther extracted with EtOAc
- washThe combined organic phases were washed with brine
- dry with materialdried over sodium sulfate
- filtrationFiltration and evaporation of the volatiles in vacuo
- customafforded a crude residue which
- customwas purified via flash column chromatography
Sources & evidence
- ORD record
- ord-a4a5ffe3ebf14fd4bded5c7d451ec43b
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652057B2
Linked notes
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