4-(4-Hydroxyphenyl)butanoic acid → 4-(4-hydroxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

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Reaktionsschritte

A mixture of 4-(4-Hydroxyphenyl)butanoic acid (0.90 g, 5 mmol), O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (0.59 g, 5 mmol) and 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (1.15 g, 6 mmol) in 50 mL dichloromethane was stirred at room temperature for 2 h (monitored by TLC). The mixture was extracted with water and dried over magnesium sulfate. The residue was purified by chromatography (MeOH:DCM=1:50) to give the title compound (0.84 g, 65%). NMR (400 MHz in DMSO, Bruker AVANCE-400): δ 1.50 (m, 3H, OTHP), 1.71 (m, 3H, OTHP), 1.73 (m, 2H, CH2), 1.96 (m, 2H, CH2), 2.44 (m, 2H, CH2), 3.48 (t, 1H, J=5.0 Hz, OTHP), 3.91 (t, 1H, J=10.0 Hz, OTHP), 4.80 (s, 1H, OTHP), 6.65 (d, 2H, J=5.0 Hz, Ar—H), 6.95 (d, 2H, J=10.0 Hz, Ar—H), 9.10 (s, 1H, NH), 10.87 (s, 1H, OH).

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