Hydrochloric Acid → 4-(3,4-dihydroisoquinolin-2(1H)-yl)-1-(4-fluorophenyl)butan-1-one

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Reaction Steps

Dioxolane 4A (2.75 g, 6.0 mmol) and 1 M HCl (15 mL) were stirred in MeOH (50 mL) at RT for 3 days. After concentration in vacuo the residue was extracted with EtOAc (400 mL) and 1 M NaOH (100 mL), then H20 (2×50 mL), and brine (25 mL). The solution was dried (Na2SO4), filtered, and concentrated to yield ketone 11A (1.9 g, quant.) as a yellow solid. 13C NMR(300 MHz, CDCl3, δ): 198.60, 165.59 (d, J=254 Hz), 134.85, 134.38, 133.56, 131.65 (d, J=9 Hz), 128.61, 126.56, 126.08, 125.56, 115.52 (d, J=22 Hz), 57.36, 56.08, 50.87, 36.14, 29.12, 21.79.

Provenance & Evidence