Thionyl Chloride → 5-(Chloromethyl)-2-methylpyridine hydrochloride
Reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>C1COCC1>[ClH:12].[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (6-methylpyridin-3-yl)methanol (1.24 g) in THF (12.4 mL) was added thionyl chloride (1.10 mL) under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the obtained residue was suspended in ethyl acetate. The precipitate was collected by filtration, and washed with ethyl acetate-hexane to give the title compound (1.64 g).
Workup
- temperaturecooling
- concentrationThe reaction mixture was concentrated under reduced pressure
- filtrationThe precipitate was collected by filtration
- washwashed with ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-2f95570a6b704641abd4e40931c3ffec
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315458B2
Reaction notes
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