Water → 2-Isobutylthiophene

Temperature

-40 °C

A solution of thiophene (6.00 g, 0.0714 mol) in 80 mL of THF (80 mL) was treated with n-BuLi (1.6 M in hexane, 54 mL, 0.0864 mol) at −78° C. The mixture was stirred at −40° C. for about 2 hours. The solution was then cooled to −78° C. again and treated with 2-methylpropyliodide (16.04 g, 0.0871 mol). The solution was stirred at 0° C. for 2 hours, and then overnight at room temperature for about 16 hours. The solution was treated with water (25 mL) and extracted with petroleum ether (3×25 mL). The organic layer was dried over magnesium sulfate and filtered. The crude product was purified by distillation (54-55° C. at 12 mmHg) to give the sub-title compound (3.0 g, 0.0213 mol) in 30% yield.

1. temperatureThe solution was then cooled to −78° C. again
2. stirringThe solution was stirred at 0° C. for 2 hours
3. waitovernight at room temperature for about 16 hours
4. extractionextracted with petroleum ether (3×25 mL)
5. dry with materialThe organic layer was dried over magnesium sulfate
6. filtrationfiltered
7. distillationThe crude product was purified by distillation (54-55° C. at 12 mmHg)

ORD record

ord-a9479445b305427c8380763ec6a38d4a

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652054B2