Water → HCID 68008844, compound

Participants

Reaction Steps

A 2-neck 1-Liter round bottom flask was equipped with a condenser, a magnetic stir bar and an addition funnel. The flask was charged with 100 mL of anhydrous ether. Lithium aluminum hydride (2.30 g) was then carefully added to the flask. 3-(9-{2-[9-(2-Ethoxycarbonyl-ethyl)-9H-fluoren-9-yl]-ethyl}-9H-fluoren-9-yl)-propionic acid ethyl ester (11.3 g, 20.2 mmol) was suspended in 100 mL of anhydrous ether and added to the addition funnel. The suspension of diester was then added dropwise to the rapidly stirred lithium aluminum hydride suspension. The addition funnel was rinsed with additional portions of anhydrous ether to rinse all of the diester into the reaction flask. The reaction mixture was then refluxed for several hours and then left at ambient temperature overnight. The rapidly stirred reaction mixture was carefully treated by the dropwise addition of water (2.3 mL), followed by 15% NaOH solution (2.3 mL), and finally more water (6.9 mL). After stirring for 2 h, the ether solution was filtered from the aluminum salts. The salts were rinsed with additional portions of diethyl ether. The combined organic portions were concentrated under reduced pressure to give a white solid. The white solid was dissolved in 100 mL of ethyl acetate, washed with 1N HCl solution, water, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting white solid was crystallized from hot toluene to give the title compound (2-d) (8.8 g) as white crystals. 1H NMR (CDCl3, 500 MHz) δ 7.73 (d, J=7.5 Hz, 4H), 7.36 (m, 4H), 7.28 (m, 4H), 7.00 (d, J=7.5 Hz, 4H), 3.15 (t, J=6.7 Hz, 4H), 1.65 (m, 4H), 1.24 (s, 4H), 0.64 (m, 4H).

Provenance & Evidence