Pyridine → n-Pentyltriflate
Reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)CCCC.[S:13]([O:20]S(C(F)(F)F)(=O)=O)([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14]>>[CH2:2]([O:20][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH2:3][CH2:4][CH2:5][CH3:6]Participants
4
Procedure
To a nitrogen flushed round bottom flask equipped with a stir bar was added pyridine (0.81 mL, 10.0 mmol) and n-pentanol (1.09 mL, 10.0 mmol). The reaction was cooled in an ice bath and triflic anhydride (1.69 mL, 10.0 mmol) was added dropwise. The ice bath was allowed to melt over two hours at which time the entire reaction mixture was filtered over a column of silica gel eluting with dichloromethane. The filtrate was carefully evaporated in vacuo then carried on without further purification(1.11 g, 5.04 mmol).
Workup
- customTo a nitrogen flushed round bottom flask equipped with a stir bar