Water → ethyl 3-(1-benzyl-3-ethoxy-1H-pyrazol-4-yl)propionate
Reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([OH:22])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:24][CH3:25].O>CN(C)C=O>[CH2:3]([N:10]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:22][CH2:24][CH3:25])=[N:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium hydride (60%, oily, 1.28 g) was added to a solution of ethyl 3-(1-benzyl-3-hydroxy-1H-pyrazol-4-yl)propionate (8.78 g) in N,N-dimethylformamide (100 ml) at 0° C., and the mixture was stirred for 30 minutes. Iodoethane (2.82 ml) was added to the reaction mixture, and the mixture was stirred at room temperature for one hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with 1N hydrochloric acid and then with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-(1-benzyl-3-ethoxy-1H-pyrazol-4-yl)propionate (8.80 g, yield: 91%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:5, volume ratio).
Workup
- stirringthe mixture was stirred at room temperature for one hour
- extractionwas extracted with ethyl acetate
- washThe ethyl acetate layer was washed with 1N hydrochloric acid
- dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-eda984ef5ea74a5086b091333cb88066
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179823B1
Reaction notes
Loading…