As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 393522-78-6, name is Methyl 4′-(hydroxymethyl)-[1,1′-biphenyl]-4-carboxylate, molecular formula is C15H14O3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. category: alcohols-buliding-blocks
To a cold solution (0 C) of HO-biphenyl-CO2Me (100 mg, 412 mumol) in CH2Cl2 (5 mL) was added Et3N (86 muL, 618 mumol) and MsCl (35 muL, 453 mumol). The reaction was allowed to stir at room temperature and after full conversion was seen on TLC (16 h), the mixture was quenched with H2O, extra CH2Cl2 was added and the organic layer was washed with water, brine, dried over MgSO4, filtrated and concentrated in vacuo. The crude product was redissolved in DMF and NaN3 (200 mg, 3.08 mmol) was added. The reaction mixture was stirred for 16 h, H2O was added and the mixture was extracted three times with EtOAc, dried over Na2SO4, filtrated and concentrated in vacuo. Column chromatography (EtOAc/Hept 1:4) yielded the product (108 mg, 98%) as white crystals. RF = 0.8 (EtOAc/Hept 1:1) 1H NMR (400 MHz, CDCl3) delta 8.03 (d, J = 8.6 Hz, 2H), 7.55 (dd, J = 12.9, 8.5 Hz, 4H), 7.40 (d, J = 8.4 Hz, 2H), 4.41 (s, 2H), 3.86 (s, 3H) ppm. 13C NMR (101 MHz, CDCl3) delta 166.89, 144.82, 140.09, 140.08, 137.39, 130.13, 129.16, 129.13, 127.60, 126.99, 77.34, 77.02, 76.70, 52.14, 45.82, 31.87, 22.68, 14.10, 1.01 ppm. FTIR = 2958, 2843, 2105, 1719, 1608, 1432, 1397, 1286, 1110, 768, 736 cm-1. HRMS (EI) calcd for C15H13N3O2 (M-N3)+ 225.0915, found 225.0896.
With the rapid development of chemical substances, we look forward to future research findings about 393522-78-6.
Reference:
Article; Wammes, Angelique E.M.; Hendriks, Tom G.; Amatdjais-Groenen, Helene I.V.; Wijdeven, Marloes A.; Van Hest, Jan C.M.; Van Delft, Floris L.; Ritschel, Tina; Rutjes, Floris P.J.T.; Bioorganic and Medicinal Chemistry; vol. 22; 20; (2014); p. 5593 – 5603;,
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