HCID 68581004, compound → Citalopram aldehyde

Participants

Reaction Steps

1-(2-[1, 3]-dioxolan-2-yl-ethyl)-1-(4-fluorophenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (6 g) was dissolved in a mixture of acetone (100 mL) and aqueous HCl (5N, 30 mL). The reaction mixture was stirred at room temperature for 60 h, and concentrated to remove acetone. The aqueous solution was extracted with ethyl acetate (40 mL), and concentrated to give a crude oil. It was dissolved in acetone (80 mL) and aqueous HCl (5N, 25 mL), stirred for 3 h, and concentrated to remove acetone. The aqueous solution was extracted with ethyl acetate (40 mL), washed with water, and concentrated to give the pure product 7 (5.6 g). 1H NMR (CDCl3, δ): 2.22-2.64 (M, 4H), 5.14 (s, 2H), 6.94-7.06 (m, 2H), 7.40-7.63 (m, 5H), 9.70 (s, 1H).

Provenance & Evidence