Ammonium Chloride → Cyclopropyl(2-methoxypyridin-4-yl)methanol
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][N:10]=1)[CH:6]=[O:7].[CH:11]1([Mg]Br)[CH2:13][CH2:12]1.[Cl-].[NH4+]>C1COCC1>[CH:11]1([CH:6]([C:5]2[CH:8]=[CH:9][N:10]=[C:3]([O:2][CH3:1])[CH:4]=2)[OH:7])[CH2:13][CH2:12]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere, to a solution of 2-methoxyisonicotinaldehyde (4.33 g) in THF (100 mL) was added 0.60 M cyclopropylmagnesium bromide (63.1 mL) at 0° C., and the mixture was stirred at 0° C. for 10 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After silica gel filtration, the solvent was evaporated under reduced pressure to give a crude product of the title compound (5.30 g) as a brown oil. This compound was used for the next step without further purification.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter silica gel filtration
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-0a63a39d38c44f4aa8ef88ad6baec502
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181186B2
Reaction notes
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