Tetrahydrofuran → HCID 20780529, 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 15 mL of anhydrous THF and 30 mL of anhydrous ether. Lithium aluminum hydride (4.80 g) was then carefully added to the flask. 3-[9-(2-Ethoxycarbonyl-ethyl)-9H-fluoren-9-yl]-propionic acid ethyl ester (18.2 g) was dissolved in 95 mL of anhydrous ether and 37 mL of anhydrous THF and this mixture was added to the addition funnel. The solution of diester was then added dropwise to the rapidly stirred lithium aluminum hydride suspension over a period of 60 min. After an additional 2 hours, the rapidly stirred reaction mixture was carefully treated by the dropwise addition of water (31 mL), followed by 35% NaOH solution (63 mL), and finally more water (66 mL). Additional diethyl ether was added to keep the slurry stirring. After stirring for 30 min, the ether/THF layer was allowed to separate and was then decanted 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 200 mL of ether and 100 mL of THF, washed with 1N HCl solution (2×75 mL) and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting white solid was crystallized from hot toluene to give the title compound (1-c) (12.3 g) as white flakes. 1H NMR (CDCl3, 500 MHz) δ 7.71 (m, 2H), 7.37-7.27 (m, 6H), 3.32 (t, J=6.4 Hz, 4H), 2.09 (m, 4H), 0.87 (m, 4H).

Provenance & Evidence