Dimethylformamide dimethyl acetal → ethyl 1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C[N:17]([CH:19](OC)OC)C.Cl.[C:25]([NH:29]N)([CH3:28])([CH3:27])[CH3:26]>C1(C)C=CC=CC=1>[C:25]([N:29]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:19]=[N:17]1)([CH3:28])([CH3:27])[CH3:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of ethyl 3-(4-fluorophenyl)-3-oxopropanoate (19.8 g, 94.20 mmol) and DMFDMA (13.76 mL, 103.61 mmol) in toluene (150 mL) was stirred at 100° C. for 14 hr, and concentrated under reduced pressure. The residue was dissolved in ethanol (150 ml), tert-butylhydrazine hydrochloride (11.74 g, 94.20 mmol) and TEA (14.44 mL, 103.61 mmol) were added thereto. The reaction mixture was stirred at 80° C. for 3 hr, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure to give ethyl 1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylate (18.67 g, 64.3 mmol, 68.3%) as a white powder.
Workup
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in ethanol (150 ml)
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate
- washthe solution was washed with water and saturated brine
- customdried
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-43f56c01d8034bebbc80d86c8a398018
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156837B2
Reaction notes
Loading…