Reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][OH:9])=[CH:5][CH:4]=[N:3]1.O[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.O1CCCC1>[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][O:9][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=[N:3]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 2-(1-methyl-1H-pyrazol-5-yl)ethanol (1.00 g), 4-hydroxybenzotrifluoride (2.57 g), 1.9 M diisopropyl azodicarboxylate (6.26 mL, toluene solution), triphenylphosphine (3.12 g) and tetrahydrofuran (50 mL) was stirred at a room temperature for 2 days. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water, and was then dried over anhydrous sodium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=90:10 to 55:45), so as to obtain the title compound (1.17 g) in the form of a light yellow oily substance.
Workup
- extractionthe obtained mixture was then extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialwas then dried over anhydrous sodium sulfate
- concentrationfollowed by vacuum concentration
- customThe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=90:10 to 55:45)
Sources & evidence
- ORD record
- ord-ad54ccf442e04ba5aae94821068c84c9
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642626B2
Linked notes
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