Tetrahydrofuran → 1-(4-Hydroxyphenyl)-2-(pyridin-4-yl)ethanone

Participants

Reaction Steps

Intermediate 1B, 1-(4-(benzyloxy)phenyl)-2-(pyridin-4-yl)ethanone (5.22 g, 17.21 mmol) and solvent THF (60 mL) were added to 20% Pd(OH)2—C, wet (1.044 g, 7.43 mmol) in a 250 mL stainless steel pressure bottle. The reaction mixture was stirred for 3 hr at 30 psi and ambient temperature. HPLC indicated that both starting material and product were present, so MeOH (10 mL) was added and the reaction was run for an additional 1 h. The reaction mixture was filtered through a nylon membrane and the filtrate was concentrated under reduced pressure to give a pale yellow solid (3.13 g, 85% yield). Much of the yellow color was removed by rinsing with MeOH. After the MeOH rinses, the solid was rinsed with Et2O, then dried in a vacuum oven at 50° C. for 4 hours. This vacuum-dried sample weighed 2.071 g (56.4%). 1H NMR (300 MHz, DMSO-d6) δ 10.38 (br s, 1H), 8.52-8.45 (m, 2H), 7.96-7.89 (m, 2H), 7.29-7.24 (m, 2H), 6.90-6.83 (m, 2H), 4.35 (s, 2H). MS (DCI—NH3) m/z=214 (M+H)+, m/z=231 (M+NH4)+.

Provenance & Evidence