Pyridine → Methyl 5-methyl-3-(((trifluoromethyl)sulfonyl)oxy)thiophene-2-carboxylate

Temperature

0 °C

Into a 100-mL round-bottom flask, was placed methyl 3-hydroxy-5-methylthiophene-2-carboxylate (1.04 g, 5.74 mmol), dichloromethane (7 mL), pyridine (1.44 mL, 17.81 mmol). This was followed by the addition of Tf2O (1.45 mL, 8.61 mmol) dropwise with stirring at 0° C. The resulting solution was stirred for 2.0 h at 0° C. in a water/ice bath. The reaction progress was monitored by GCMS. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×15 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 2×20 mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:9). This resulted in 1.74 g (99%) of methyl 5-methyl-3-(((trifluoro methyl)sulfonyl)oxy)thiophene-2-carboxylate as yellow oil.

1. customInto a 100-mL round-bottom flask, was placed
2. stirringThe resulting solution was stirred for 2.0 h at 0° C. in a water/ice bath
3. customThe reaction was then quenched by the addition of 10 mL of water
4. extractionThe resulting solution was extracted with 3×15 mL of dichloromethane
5. washThe resulting mixture was washed with 2×20 mL of sodium chloride
6. dry with materialThe mixture was dried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum
8. customThis resulted in 1.74 g (99%) of methyl 5-methyl-3-(((trifluoro methyl)sulfonyl)oxy)thiophene-2-carboxylate as yellow oil

ORD record

ord-2f2f7e8d57014d299cbb69c75e5eb49d

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1