[Synthesis]
GENERAL METHODS: Ethanol (1.0 mL) was added to a suspension of 3-(4-hydroxyphenyl)propanoic acid (0.05 mmol) and trimethylchlorosilane (TMCS, 0.1 mmol), and the reaction mixture was stirred at 25 °C for 24 h. The reaction was completed by evaporation of the solvent. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure to afford ethyl 3-(4-hydroxyphenyl)propionate (1b) in quantitative yield without further purification. The product was an oil; 1H NMR (400 MHz, CDCl3): δ 1.13 (3H, m, CH3), 2.82 (2H, m, CH2), 2.88 (2H, m, CH2), 4.00 (2H, m, OCH2), 6.75 (2H, m, Ph-H), 7.06 (2H, m, Ph-H); 13C NMR (50 MHz, CDCl3): δ 14.20 (CH3), 30.12 (CH2), 35.10 (CH2), 60.10 (CH2), 115.45 (2CH), 129.48 (2CH), 131.75 (C), 155.43 (C), 172.10 (CO); MS (EI): m/z 266; elemental analysis: Calculated values C, 68.02; H, 7.27; O, 24.71, measured values C, 68.0; H, 7.26; O, 24.68. |
[References]
[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5345 - 5351
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1495 - 1503
[3] Tetrahedron Letters, 2010, vol. 51, # 44, p. 5753 - 5756
[4] Molecules, 2018, vol. 23, # 2,
[5] Patent: US2010/298422, 2010, A1. Location in patent: Page/Page column 18 |