New learning discoveries about Methyl 3-(4-(benzyloxy)phenyl)propanoate

24807-40-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-((4-((phenylmethyl)oxy)phenyI)methyl)-4-pentenoate(33.1); To a solution of lithium diisopropylamide (6.5 mL, 13.0 mmol, 2.0M in heptanelambdaTHF/ethylbenzene) in THF (25.0 mL) and l,3-dimethyl-3,4,5,6- tetrahydro-2(lH)-pyrimidinone (5.0 mL) was slowly added methyl 3-(4- (benzyloxy)phenyl)propanoate 23.1 (3.00 g, 1 1 mmol) in THF (10 mL) and 1 ,3- dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (2.5 mL) at -780C. The resulting mixture was stirred at -780C for 30 minutes and then allyl iodide (1.08 mL, 13.0 mmol) in THF (5.0 mL) was added. The reaction mixture was stirred at the same temperature for 20 minutes. The reaction was then stirred at room temperature for 16 hours. The reaction was quenched with water (30.0 mL). The solvent was concentrated in vacuo, and the residue was disolved in EtOAc (100 mL) and washed with brine (2 x 25 mL) and then dried with Na2SO4. The product thus obtained was purified on a silica gel column, to give the title compound 33.1. 1H NMR (500 MHz, CDCl3) delta ppm 2.29 – 2.34 (m, 1 H) 2.39 – 2.44 (m, 1 H) 2.63 – 2.79 (m, 2 H) 2.91- 2.96 (m, 1 H) 3.64 (s, 3 H) 5.06 – 5.18 (m, 4 H) 5.67 – 5.85 (m, 1 H) 6.88 – 7.03 (m, 2 H) 7.03 – 7.18 (m, 2 H) 7.34 – 7.49 (m, 5 H).

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Reference:
Patent; AMGEN INC.; WO2008/130514; (2008); A1;,
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