Water → methyl (E)-3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)benzoate
Reaction equation
[CH2:1]([C:4]1[C:5](Cl)=[N:6][CH:7]=[C:8]([C:10]([O:19][CH2:20][O:21][CH3:22])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])[CH:9]=1)[CH:2]=[CH2:3].[H-].[Na+].[CH3:26][O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=1.O>CN(C)C=O>[F:12][C:11]([F:14])([F:13])[C:10]([C:8]1[CH:9]=[C:4](/[CH:1]=[CH:2]/[CH3:3])[C:5]([O:35][C:31]2[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=2)[C:28]([O:27][CH3:26])=[O:36])=[N:6][CH:7]=1)([O:19][CH2:20][O:21][CH3:22])[C:15]([F:18])([F:17])[F:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 3-allyl-2-chloro-5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)pyridine (80 mg, 0.220 mmol) in N,N-dimethylformamide (2 mL), sodium hydride (14.4 mg, 0.330 mmol) and 3-hydroxybenzoic acid methyl ester (50 mg, 0.330 mmol) were added under ice-cold conditions, and the resultant mixture was stirred at 80° C. for 18 hours and further stirred at 100° C. for 3 hours. The reaction solution was added with water under room temperature and extracted with ethyl acetate. The organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and the title compound (81 mg, yield 76.5%) was obtained as a colorless oil.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- customdried
- concentrationconcentrated in vacuo
- customThe obtained residue was purified
Sources & evidence
- ORD record
- ord-bb683a28b36d48538b7fdb3fb2729e97
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153634B2
Reaction notes
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