Magnesium Bromide → HCID 10928895, compound

Participants

Reaction Steps

Magnesium bromide etherate (0.194 g, 0.75 mmol) was dissolved in 20 ml ether in a two-necked flask under oxygen-free nitrogen atmosphere at room temperature. After stirring for 1 hour, 2-(p-chlorophenylmethylene)-3-[p-(2-morpholinoethoxy)phenyl]-6-methoxy- 2,3-dihydrobenzo[b]furan-3-ol (5) (0.247 g, 0.5 mmol) in ether (10 ml) was added dropwise to the mixture. After stirring for 4 hours, LiAlH4 (0.076 g, 2.0 mmol) was added to the above reaction mixture. The reaction mixture was left overnight at room temperature. After stirring overnight, ethyl acetate was added dropwise till hydrogen evolution ceased. The above mixture was washed with water followed by brine (2×20 ml), dried (anhydrous magnesium sulfate) and the solvent was evaporated off to give an oil which was chromatographed on silica. Elution with (chloroform: hexane: triethylamine=1:1:0.2) yielded a white solid of the free base (Rf =0.4). Yield (60%); m.p. 126°-128° C.; 1H-NMR (CDCl3) (δ) 2.60-2.63 (m, 4H, N(CH2CH2)2O (ring)), 2.85 (t, 2H, OCH2CH2N), 3.74-3.77 (m, 4H, N(CH2CH2)2O (ring)), 3.84 (s, 3H, OCH3), 4.11 (CH2 at C-2), 4.17 (t, 2H, OCH2CH2N), 6.84-7.44 (m, 11H, ArH); m/z (%) 479 (10), 491 (35), 100 (100).

Provenance & Evidence