Trimethyltin chloride → HCID 90013739, compound

n-BuLi (1.6 M, 42 mL, 67 mmol) was added slowly to a solution of 2-tetradecyl-thiophene (17.0 g, 237 mmol) in THF (150 mL) at −78° C. and stirred for 30 min. Trimethyltin chloride (13.3 g, 67 mmol) in THF (30 mL) was added dropwise to the resultant suspension and then gradually warmed to room temperature. The reaction mixture was stirred for 18 h and quenched with saturated ammonium chloride solution (100 mL). The mixture was extracted with diethyl ether (2×100 mL) and the combined organic extracts were washed with brine (100 mL). The organic phase was dried and concentrated to give brown oil (26.8 g, 99%), which was used directly in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.02 (d, 1H, J=3.2 Hz), 6.90 (d, 1H, J=3.2 Hz), 2.85 (t, 2H, J=8 Hz), 1.68 (q, 2H, J=7.6 Hz), 1.50-1.20 (m, 22H), 0.88 (t, 3H, J=6.8 Hz), 0.344 (s, 9H).

1. stirringThe reaction mixture was stirred for 18 h
2. customquenched with saturated ammonium chloride solution (100 mL)
3. extractionThe mixture was extracted with diethyl ether (2×100 mL)
4. washthe combined organic extracts were washed with brine (100 mL)
5. customThe organic phase was dried
6. concentrationconcentrated

ORD record

ord-5c69c1295ab8480197885cfaad82b545

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09231215B2