Ammonium Chloride → ethyl 3-[cyclopropyl(hydroxy)methyl]-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate
Reaction equation
[CH:1]([C:3]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]([CH3:17])[N:4]=1)=[O:2].[CH:18]1([Mg]Br)[CH2:20][CH2:19]1.[Cl-].[NH4+]>O1CCCC1>[CH:18]1([CH:1]([OH:2])[C:3]2[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]([CH3:17])[N:4]=2)[CH2:20][CH2:19]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1.82 g (7.28 mmol) of ethyl 3-formyl-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate in 80 ml of tetrahydrofuran is admixed under argon at −78° C. with 17.5 ml (8.73 mmol) of 0.5M cyclopropylmagnesium bromide solution in tetrahydrofuran, and stirred for 30 minutes at this temperature and then overnight at room temperature. The reaction solution is admixed with saturated ammonium chloride solution and extracted with ethyl acetate, and the organic phase is dried over sodium sulphate and concentrated by evaporation on a rotary evaporator. Chromatographic purification on silica gel gives 0.67 g of ethyl 3-[cyclopropyl(hydroxy)methyl]-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate (31%).
Workup
- customovernight
- customat room temperature
- extractionextracted with ethyl acetate
- dry with materialthe organic phase is dried over sodium sulphate
- concentrationconcentrated by evaporation on a rotary evaporator
- customChromatographic purification on silica gel
Sources & evidence
- ORD record
- ord-13a55ff53c04491ba6871ee95f5c753c
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946234B2
Reaction notes
Loading…