Dimethylformamide → Tetradecyl-2-formylthiophene-3-carboxylate

Temperature

-78 °C

To a 100 mL Schlenk flask were added 0.5 mL of diisopropyl amine and 20 mL of dry THF. The flask was cooled to −78° C. 3.5 mmol of n-butyl lithium in hexane was then added to the above solution. The mixture was stirred at −78° C. for 30 minutes. After stirring, 1.0 g of tetradecylthiophene-3-carboxylate in 10 mL THF was added dropwise to the solution. After stirring at −78° C. for another 2 hours, 0.7 mL of DMF was syringed into the reaction mixture. The reaction mixture was stirred for 5 h at −78° C. and 1 mL of acetic acid was added to the flask. The mixture was poured into a separation funnel and diethyl ether was added to the mixture. The organic layer was washed 3 times with 100 mL of water, dried with MgSO4, and the solvents were removed by rotary evaporation. The resulting residue was purified by column chromatography using a mixture of hexane and dichloromethane to give the desired compound. The NMR data were obtained and were consistent with those of the desired compound.

1. stirringAfter stirring
2. stirringAfter stirring at −78° C. for another 2 hours
3. stirringThe reaction mixture was stirred for 5 h at −78° C.
4. additionThe mixture was poured into a separation funnel
5. washThe organic layer was washed 3 times with 100 mL of water
6. dry with materialdried with MgSO4
7. customthe solvents were removed by rotary evaporation
8. customThe resulting residue was purified by column chromatography
9. additiona mixture of hexane and dichloromethane

ORD record

ord-fa7559aed06e47e5b98fcfcb0b1791e9

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09337358B2