Hexane → Stannane, [2,2'-bithiophen]-5-yltrimethyl-

Temperature

0 °C

To a 3-necked flask equipped with a glass stopper, rubber septum and a nitrogen inlet was added 2,2′-bithiophene (10 g, 60.1 mmol) and anhydrous THF (100 mL). The dark (green) solution was cooled to 0° C. A 2.5 M solution of n-BuLi in hexane (26.4 mL, 66 mmol) was added via syringe. The reaction mixture was then stirred at 25° C. for 1.5 hours. The mixture was cooled to −78° C. and a 1.0 M solution of trimethylstannyl chloride in THF (66 mL, 66 mmol) was added slowly via syringe. The reaction mixture was allowed to warm to 25° C. and was stirred overnight. THF was removed in vacuo and the residue was dissolved in pentane (200 mL). The pentane layer was washed with water (3×200 mL), dried over MgSO4, and the pentane was removed in vacuo to yield a green oil. The oil was purified by vacuum distillation (118-120° C., 0.6 mmHg) to yield 12.5 g (64%) of product MS=330.

1. customTo a 3-necked flask equipped with a glass stopper, rubber septum and a nitrogen inlet
2. temperatureThe mixture was cooled to −78° C.
3. temperatureto warm to 25° C.
4. stirringwas stirred overnight
5. customTHF was removed in vacuo
6. dissolutionthe residue was dissolved in pentane (200 mL)
7. washThe pentane layer was washed with water (3×200 mL)
8. dry with materialdried over MgSO4
9. customthe pentane was removed in vacuo
10. customto yield a green oil
11. distillationThe oil was purified by vacuum distillation (118-120° C., 0.6 mmHg)

ORD record

ord-432b9a573a294b69a32f61bf78aea977

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07803885B2