Boron trifluoride → HCID 18624266, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-ethylphenyl)-2-adamantanol (1.82 g, 7.14 mmol) in dry CHCl3 (5 mL) under argon, was treated with trimethylsilyl cyanide (1.00 mL, 7.5 mmol), cooled to 0° C., treated with BF3 etherate (1.10 mL, 8.57 mmol), allowed to warm to room temperature and stirred for 2 h. The mixture was treated with dilute NaHCO3 (10 mL), extracted with CHCl3 (2×10 mL), the combined extracts washed with water (10 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; heptane-EtOAc (9:1)] to give the product (217 mg, 82%) as a colourless oil: IR νmax (thin film)/cm−1 2922, 2860, 2226, 1604, 1487, 1453, 1105, 799 and 704; NMR δH (400 MHz, CDCl3) 1.24 (3H, t, J 7.5 Hz), 1.62-1.65 (2H, m), 1.70-1.82 (5H, m), 1.98-2.04 (3H, m), 2.45 2.48 (2H, m), 2.66 (2H, q, J 7.5 Hz), 2.79 (2H, s), 7.15 (1H, d, J 7.5 Hz) and 7.25-7.34 (3H, m); Anal. Calcd for C19H23N: C, 85.99; H, 8.73; N, 5.28. Found: C, 85.85; H, 8.77; N, 5.23.

Provenance & Evidence