Thiophene → 2-Hexylthiophene

To a solution of thiophene (15 g, 0.178 mole) in 200 mL of dry THF at −78° C., n-BuLi (103 mL, 0.165 mol, 1.6M hexane) was added. The reaction mixture was warmed to RT and stirred for 1 h. After the mixture was cooled to −78° C., 23.15 mL (0.165 mole) of 1-bromohexane was added. The solution was warmed from −78° C. to RT and was stirred overnight. At the end of the reaction, the mixture was poured into ice water, the aqueous layer was extracted with ether, and the organic layer was dried over anhydrous MgSO4. The solvent was removed by rotary evaporation. The residue was redistilled under vacuum to get a colorless liquid (yield=75%). 1H-NMR (300 MHz, CDCl3) δ 7.12 (dd, 1H), 6.92-6.97 (m, 1H), 6.8 (dd, 1H). 2.8 (t, 2H), 1.6-1.9 (q, 2H), 1.30-1.49 (m, 6H), 0.82 (t, 3H).

1. temperatureAfter the mixture was cooled to −78° C.
2. temperatureThe solution was warmed from −78° C. to RT
3. stirringwas stirred overnight
4. customAt the end of the reaction
5. extractionthe aqueous layer was extracted with ether
6. dry with materialthe organic layer was dried over anhydrous MgSO4
7. customThe solvent was removed by rotary evaporation
8. distillationThe residue was redistilled under vacuum

ORD record

ord-fd6aa4a1862e45209729fedb8fd76397

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618298B2