Thionyl Chloride → 4-t-Butyl-2-(1-chloroethyl)-pyridine
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH:11](O)[CH3:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:16])=O>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH:11]([Cl:16])[CH3:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-t-Butyl-2-(1-hydroxyethyl)-pyridine (3.6 g, 20.1 mmole) is dissolved in 60 ml dichloromethane in a 200 ml one neck round bottom flask under nitrogen. The solution is cooled to 0° C., is treated with thionyl chloride (2.2 ml, 30 mmole) in 10 ml dichloromethane, and the reaction is stirred 1 h at 0° C. followed by 2 h at room temperature. The reaction is quenched with 1×75 ml saturated sodium bicarbonate, the layers are separated and the aqueous layer is extracted with 3×25 ml dichloromethane. The combined organics are dried over potassium carbonate and are concentrated in vacuo to give 3.9 g (98%) of 4-t-Butyl-2-(1-chloroethyl)-pyridine as a yellow oil.
Workup
- waitfollowed by 2 h at room temperature
- customThe reaction is quenched with 1×75 ml saturated sodium bicarbonate
- customthe layers are separated
- extractionthe aqueous layer is extracted with 3×25 ml dichloromethane
- dry with materialThe combined organics are dried over potassium carbonate
- concentrationare concentrated in vacuo
Sources & evidence
- ORD record
- ord-cbed1e7569cf48428cc4341d52a8c061
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06043248
Reaction notes
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