三苯基膦作为缩合剂进行苯甲酸化

8 mmol, 0.50 g) in one portion. The reaction mixture containing 0.25 mmol of 40was thereafter set aside at roomtemperature while a new solution was being prepared: 3-Aminophenol (2.5 mmol, 0.28 g) and pyridine (3.20 mmol, 0.26 g) was dissolved in THF (5 ml). The mixture was cooled to about -25 ℃(ethanol/granular CO2), and vigorously stirred while the ready-made solution of 40was added dropwise. The cooling bath was removed after a few minand the temperature allowed to rise towards room temperature. Most of the solvents were removed under reducedpressure and the product purified by flash chromatography on Merck No. 9385 silica gel60, using ether as eluent. Removal ofthe solvent gave N -(3-hydroxyphenyl)-hexanamide 41(0.52 g, 98 %) as a colourless solid, m.p. 139-140 ℃. 1 H NMR (200 MHz, acetone-d6): δ0.90 (m, 3H, CH3), 1.35 (m, 4H, CH2), 1.65(m, 2H, CH2), 2.35 (t, 2H, CH2), 6.52 (m, IH, H ~o,~), 7.0 (m, 2H, H~om.), 7.42(s, 1H, H~o), 8.4 (s, 1H, OH), 9.05 (s, 1H, NH); MS (70 eV): m/z(%) 207 (17, M + ),151 (6.5), 109 (100).

【 Tetrahedron lett. 1997, 5359】

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