Thiophene → HCID 525987, compound

Participants

Reaction Steps

n-BuLi (1.6 M, 48 mL, 76 mmol) was added dropwise to a solution of thiophene (7.0 g, 83 mmol) in THF (70 mL) at −78° C. and stirred for 45 min. Tetradecyl bromide (23 mL, 76 mmol) in THF (25 mL) was added dropwise to the resultant suspension and then gradually warmed to room temperature and stirred for 18 h. The reaction mixture was quenched with water (60 mL) and extracted with diethyl ether (2×100 mL). The combined organic extracts were dried over MgSO4 and concentrated to give brown oil (20.7 g, 97%), which was used directly in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.10 (d, 1H, J=5.2 Hz), 6.91 (dd, 1H, J=5.7, 4.4 Hz), 6.77 (d, 1H, J=3.2 Hz), 2.82 (t, 2H, J=7.6 Hz), 1.68 (q, 2H, J=6.8 Hz), 1.50-1.20 (m, 22H), 0.88 (t, 3H, J=6.8 Hz).

Provenance & Evidence