Perfluoro-1-butanesulfonyl fluoride → 2-Pyrazinecarboxylic acid, 5-(fluoromethyl)-, methyl ester
Reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1.F.F.F.C(N(CC)CC)C.[F:23]C(F)(C(F)(F)F)C(F)(F)C(F)(F)S(F)(=O)=O.C([O-])(O)=O.[Na+]>C1COCC1.C(N(CC)CC)C>[F:23][CH2:2][C:3]1[N:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 5-(hydroxymethyl)pyrazine-2-carboxylate (0.64 g) in THF (20 mL) was added triethylamine (2.30 g) and the solution was cooled to 0° C. Triethylamine trihydrofluoride (1.22 g) was then added followed by nonafluorobutanesulfonyl fluoride (2.28 g) dropwise over 5 mins. After warming to RT and stirring for 2 h, NaHCO3 (sat., aq., 100 mL) was added, and the mixture was extracted with EtOAc (2×50 mL). The combined organic portions were dried over MgSO4, evaporated, and purified by silica gel chromatography (5% to 50% EtOAc in hexane) to afford the title compound (94 mg). 1H NMR (400 MHz, CDCl3) δ ppm 4.07 (s, 3 H), 5.67 (d, J=46.5 Hz, 2 H), 8.89 (s, 1 H), 9.28 (s, 1 H)
Workup
- temperatureAfter warming to RT
- extractionthe mixture was extracted with EtOAc (2×50 mL)
- dry with materialThe combined organic portions were dried over MgSO4
- customevaporated
- custompurified by silica gel chromatography (5% to 50% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-27b2f457972741da869c6d1cb0ffc386
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940734B2
Reaction notes
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