Hydrochloric Acid → 1-[5-(1-Methylethoxy)pyridin-2-yl]ethanol
Reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[O:12])=[N:9][CH:10]=1)[CH3:3].[CH3:13][Mg]Br.Cl>O1CCCC1>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([OH:12])[CH3:13])=[N:9][CH:10]=1)[CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5-(1-Methylethoxy)picolinaldehyde (24 mg, 0.145 mmol) was dissolved in tetrahydrofuran (1.5 mL). The resultant mixture was added with methylmagnesium bromide (230 μL, 0.218 mmol) under ice-cold conditions, stirred at 0° C. for 30 minutes, and further stirred at room temperature for 30 minutes. The reaction solution was added with 1N aqueous solution of hydrochloric acid, an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and 1-[5-(1-methylethoxy)pyridin-2-yl]ethanol (27 mg, yield 98%) was obtained as a brown oil.
Workup
- stirringfurther stirred at room temperature for 30 minutes
- extractionan aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe obtained residue was purified
Sources & evidence
- ORD record
- ord-3238d435f62d43268612983ae91c35a7
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153634B2
Reaction notes
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