10309-37-2

17015-63-3

17015-60-0

General procedure for the synthesis of (E)-4-(3,7-dimethyl-3-vinyl-octa-1,6-dien-1-yl)phenol from the compound (CAS: 17015-63-3): to a 5 mL solution of ether (Et2O) containing 151 mg (0.56 mmol) of the raw material, 0.28 mL (0.84 mmol, 3.0 M in Et2O ) of methylmagnesium iodide (MeMgI) ether solution. After completion of the reaction, the solvent was removed under reduced pressure and the residue was heated at 180 °C for 10 min under argon (Ar) protection. After the reaction mixture was cooled to room temperature, the reaction was quenched with 10 mL of saturated aqueous ammonium chloride (NH4Cl). Subsequently, the product was extracted with ethyl acetate (AcOEt, 10 mL x 3). The organic phases were combined, washed with brine and dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure and the crude product was purified by column chromatography (eluent: petroleum ether/ethyl acetate = 15:1) to afford psoralen as a colorless oil (129 mg, 90% yield). Thin layer chromatography (TLC) showed an Rf value of 0.53 (Expander: petroleum ether/ethyl acetate = 10:1). The specific optical rotation [α]D27.5 was +24.9 (c 0.98, CHCl3). Nuclear magnetic resonance hydrogen spectrum (1H NMR, 400 MHz, CDCl3) δ: 7.24 (d, J=8.5 Hz, 2H), 6.76 (d, J=8.5 Hz, 2H), 6.25 (d, J=16.2 Hz, 1H), 6.05 (d, J=16.2 Hz, 1H), 5.88 (dd, J=17.2,10.8 Hz, 1H ), 5.11 (t, J=7.1 Hz, 1H), 5.02 (m, 2H), 1.95 (m, 2H), 1.67 (s, 3H), 1.58 (s, 3H), 1.49 (m, 2H), 1.19 (s, 3H). Nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, CDCl3) δ: 154.5, 145.9, 135.7, 131.3, 130.7, 127.3, 126.4, 124.7, 115.3, 111.8, 42.4, 41.2, 25.6, 23.2, 23.1, 17.6. electrospray mass spectrometry (ESI- MS): calculated value C18H25O+ [M+H]+: 257.1, measured value: 257.2.