Carbon tetrabromide → Cis-1-Bromo-tetradec-6-ene

Beteiligte Stoffe

Reaktionsschritte

Alcohol 7 (115 mg, 0.541 mmol) in dichloromethane (100 ml) at 0° C. was treated successively with carbon tetrabromide (395 mg, 1.20 mmol) and triphenylphosphine (312 mg, 1.20 mmol), and allowed to warm to room temperature with stirring over 2 h. The reaction mixture was triturated with water and extracted with methylene chloride, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash column chromatography using hexanes as an eluent, thus affording pure 8 as a light oil (105 mg, 0.381 mmol, 70%); δH(270 MHz, CDCl3); 0.87 (3H, t, J=6.1 Hz), 1.1-1.65 (14H, m), 1.85 (2H, quin, J 7.0), 2.03 (4H, m), 3.4 (2H, t, J 6.8) and 5.35 (4H, m); δC(67.5 MHz, CDCl3) 27.06, 27.32 27.72, 27.91, 28.04, 28.96, 29.32, 29.37, 29.71, 29.83, 31.96, 32.82, 34.01, 129.31, 130.47.

Herkunft & Nachweise