Allyl iodide → 3-Allyl-2-chloro-5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)pyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:17][CH2:18][O:19][CH3:20])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH2:21]([Li])[CH2:22][CH2:23]C.C(I)C=C.[Cl-].[NH4+]>O1CCCC1.O>[CH2:23]([C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([C:8]([O:17][CH2:18][O:19][CH3:20])([C:9]([F:12])([F:11])[F:10])[C:13]([F:14])([F:15])[F:16])[CH:6]=1)[CH:22]=[CH2:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-chloro-5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)pyridine (50 mg, 0.155 mmol) in tetrahydrofuran (2 mL), butyllithium (71 μL, 1.70 mmol) was added under −78° C. and the resultant mixture was stirred for 0.5 hour. Allyl iodide (71 μL, 0.773 mmol) was added under −78° C. and the resultant mixture was stirred at room temperature for 1 hour. The reaction solution was added with a saturated aqueous solution of ammonium chloride and 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 (36 mg, yield 64%) was obtained as a yellow 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-b099cdcbcff64ccbaa7dbc26c2495a71
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153634B2
Reaction notes
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