Pyridine → 2-(((Trifluoromethyl)sulfonyl)oxy)acetic acid methyl ester
Reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[C:16]([O:20][CH3:21])(=[O:19])[CH2:17]O.N1C=CC=CC=1>C(Cl)Cl>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][CH2:17][C:16]([O:20][CH3:21])=[O:19])(=[O:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of triflic anhydride (3.7 ml, 20.0 nmmol) in methylene chloride (10 ml) at -5° C. under argon, was added dropwise over 30 minutes a solution of methyl glycolate (1.8 g, 20.0 mmol), pyridine (1.55 ml, 20.0 mmol), and anhydrous methylene chloride (5 ml). The reaction was allowed to stir at between 0°-5° C. for 1.5 h. The mixture was then washed with water several times. The organic extract was then washed with water, brine, and dried (MgSO4). After removing the solvent under reduced pressure, flash chromatography of the residue (silica gel, methylene chloride) afforded the title compound as a colorless oil (3.0 g, 68%).
Workup
- washThe mixture was then washed with water several times
- extractionThe organic extract
- washwas then washed with water, brine
- dry with materialdried (MgSO4)
- customAfter removing the solvent under reduced pressure, flash chromatography of the residue (silica gel, methylene chloride)
Sources & evidence
- ORD record
- ord-9d9a450717f040f39685c3d8b5718813
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05929106
Reaction notes
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