Methyl iodide → Methyl 2-methylthiophene-3-carboxylate

To a solution of 3.30 g (23.2 mmol) of 2-methyl-3-thiophenecarboxylic acid in 100 ml of acetone was added 16.04 g (116.1 mmol) of anhydrous potassium carbonate and 16.47 g (7.2 ml, 116.1 mmol) of methyl iodide. The reaction mixture was allowed to stir at room temperature for 20.25 hours. A white precipitate formed. The white precipitate was filtered, washed with ethyl ether and discarded. The filtrate was concentrated in vacuo, partitioned between 250 ml of water and 250 ml of pentane and the layers separated. The organic phase was washed with a saturated solution of Na2 SO3, dried over Na2SO4, filtered and concentrated by rotary evaporation to give the title compound as a yellow oil which was used without further purification.

1. customA white precipitate formed
2. filtrationThe white precipitate was filtered
3. washwashed with ethyl ether
4. concentrationThe filtrate was concentrated in vacuo
5. custompartitioned between 250 ml of water and 250 ml of pentane
6. customthe layers separated
7. washThe organic phase was washed with a saturated solution of Na2 SO3
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated by rotary evaporation

ORD record

ord-f0e095931d8e4f92a165c8f6d8ef0fcf

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05696162