HCID 18988257, compound → HCID 18988286, compound

Participants

Reaction Steps

Part D. A solution of the ester prepared in Part C above (4.00 g, 13.6 mmol) in tetrahydrofuran (20 mL) was added dropwise to an ice-cooled solution of lithium aluminum hydride (30 mmol) in tetrahydrofuran (30 mL).The ice bath was removed, and the mixture was warmed to ambient temperaturefor 14 hours. The solution was then recooled to 0° C., and quenched by the slow addition of 1 mL water, 3 mL 15% sodium hydroxide, and 3 mL water. The resulting mixture was filtered through a plug of celite, and the filtrate was dried over anhydrous potassium carbonate, filtered and evaporated. The residue was separated by flash chromatography (1:4 ethyl acetate-hexane) to afford the product, 2-(3,4-dimethoxybenzyl)-1-hexanol, as an oil (3.39 g, 13.4 mmol, 99%). 1H NMR (CDCl3): δ 6.81-6.70 (3H, m); 3.87 (3H, s); 3.86 (3H, s); 3.54 (2 H, t, J=5.1 Hz); 2.59 (2H, d, J=7.0 Hz); 1.80-1.71 (1H, m); 1.39-1.17 (7H, m); 0.89 (3H, t,J=7.0 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 254 (5%); 253 (33%); 235 (100%); 151 (43%).

Provenance & Evidence