Hydrochloric Acid → Cyclopropyl(2-((methoxymethoxy)methyl)pyridin-4-yl)methanone
Reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][N:13]=1)[C:9]#N.[CH:14]1([Mg]Br)[CH2:16][CH2:15]1.Cl.[OH-:20].[Na+]>C1COCC1>[CH:14]1([C:9]([C:8]2[CH:11]=[CH:12][N:13]=[C:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])[CH:7]=2)=[O:20])[CH2:16][CH2:15]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere, to a solution of 2-((methoxymethoxy)methyl)isonicotinonitrile (1.87 g) in THF (20 mL) was added 0.70 M cyclopropylmagnesium bromide (30 mL) at 0° C., and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added 1N hydrochloric acid (50 mL) at 0° C., and the mixture was stirred at room temperature for 15 min. The reaction mixture was neutralized with aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.20 g) as an orange oil.
Workup
- stirringthe mixture was stirred at room temperature for 15 min
- extractionextracted with ethyl acetate
- washThe extract was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-291c3e1a13f94a88b15c1ca1fc218993
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382188B2
Reaction notes
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