Pyridine → HCID 86757608, compound
Reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[C:16]([O:25][CH3:26])(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19].N1C=CC=CC=1.C1(C)C=CC=CC=1>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:18]1([OH:19])[CH:20]=[CH:21][CH:22]=[CH:23][CH:17]1[C:16]([O:25][CH3:26])=[O:24])(=[O:5])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
Trifluoromethanesulfonic anhydride (28.4 mL, 169 mmol, 1.1 eq) was added to a solution of methyl salicylate (20 mL, 154 mmol) and pyridine (31 mL, 385 mmol, 2.5 eq) in dichloromethane (150 mL) maintained at an internal temperature about −40° C., under nitrogen. Once the addition was complete, the mixture was allowed to warm to ambient temperature and stirred for 16 hours. Toluene (150 mL) was added causing precipitation. The solids were removed by filtration and washed with toluene (20 mL). The organic solutions were combined and washed with 2 N HCl (aq) (2×50 mL), water (100 mL), saturated aqueous sodium carbonate solution (100 mL) and brine (100 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. Yield 41.93 g, 96%
Workup
- additionOnce the addition
- temperatureto warm to ambient temperature
- customprecipitation
- customThe solids were removed by filtration
- washwashed with toluene (20 mL)
- washwashed with 2 N HCl (aq) (2×50 mL), water (100 mL), saturated aqueous sodium carbonate solution (100 mL) and brine (100 mL)
- dry with materialThe organic layer was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-75d0ab024e5e4c2798641257eb7a8b34
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06320068B1
Reaction notes
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