Dimethylformamide → HCID 19920598, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-adamantyl-5-iodoanisole (1.29 g, 3.51 mmol) in anhydrous THF (50 mL) was cooled to -78° C. under argon and treated with t-butyllithium solution (4.34 mL, 1.7 M in pentane, 7.37 mmol). The reaction mixture was stirred at -78° C. for 20 min. and then treated with anhydrous N,N-dimethylformamide (0.28 g, 3.86 mmol). The reaction mixture was allowed to warm to room temperature, and was poured into a separatory funnel containing diethyl ether and saturated ammonium chloride solution. The layers were agitated and separated, and the organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified by column chromatography on silica gel (elution with 1:1 methylene chloride/hexanes) to afford 0.38 g (43% yield) of 4-(1-Adamantyl)-3-methoxybenzaldehyde as a white solid; 1H NMR (300 MHz, CDCl3) δ 9.92 (s, 1H, CHO), 7.37 (m, 3H, ArH), 3.88 (s, 3H, OCH3), 2.08 (s, 9H, adamantyl), and 1.76 (s, 6H, adamantyl); 13C NMR (75 MHz, CDCl3) δ 192.04 (C=O), 159.38, 146.00, 135.36, 127.06, 124.45, 109.54, 55.09 (OCH3), 40.15, 37.79, 36.95, and 28.90; IR (KBr) 2965, 2900, 2850, 1690 (C=O), 1250, 1160, 1135, 1035, and 1025 cm-1 ; MS (DCI) m/e 271 (MH+), 135 (C10H15+) . Anal. Calcd for C18H22O2.0.015 H2O: C, 79.88; H, 8.21. Found: C, 79.48; H, 8.34.

Provenance & Evidence