With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1271-51-8,Vinylferrocene,as a common compound, the synthetic route is as follows.
In anhydrous THF (1 mL) was dissolved 6 molpercent Cu(OAc) 2 (10.9 mg,0.066 mmol) and 6.6 molpercent of ligand (R)-DTBM-SEGPHOS (78 mg,0.060 mmol). The mixture was stirred for 15 min at r.t., then DMMS(0.5 mL, 4 equiv, 4 mmol) was added dropwise and stirring was con-tinued for 10 min at the same temperature. The solution of amine 7(381 mg, 1.2 mmol) and vinylferrocene 4 (212 mg, 1 mmol) was thenadded by using Schlenk techniques to the tube containing the solu-tion of [L*CuH] complex. The reaction mixture was stirred at 40 ¡ãCovernight, then the mixture was diluted with EtOAc (5 mL) and 5percentsolution of Na 2 CO 3 (5 mL) was added dropwise. The solution was ex-tracted with EtOAc (3 ¡Á 25 mL), the collected organic layers werewashed with brine (25 mL), dried over Na 2 SO 4 , filtrated, and the sol-vent was removed under reduced pressure to afford the crude prod-uct. The crude product was purified by chromatography on SiO 2 (hex-anes/EtOAc, 30:1 + 1percent Et 3 N; R f = 0.4) to afford target product 8.Yield: 68 mg (18percent); orange solid; mp 62?65 ¡ãC; [alpha] D20 ?14.5 (c 1.00,CHCl 3 ); HPLC analysis (Chiralcel OD-H; hexane/ i PrOH, 99:1; 0.8mL/min; 254 nm) indicated 20percent ee: t R = 5.9 (major), 6.5 (minor) min.IR (ATR): 1234, 1103, 1068, 1022, 998, 822, 749, 728, 697, 514, 487cm ?1 .1 H NMR (600 MHz, CDCl 3 ): delta = 7.39 (d, J = 7.4 Hz, 4 H, -Ph), 7.31 (t, J =7.6 Hz, 4 H, -Ph), 7.23 (t, J = 7.3 Hz, 2 H, -Ph), 4.27?4.27 (m, 1 H, Fc),4.18?4.14 (m, 3 H, Fc), 4.02 (s, 5 H, Cp Fc ), 3.81 (q, J = 6.9 Hz, 1 H, H alpha ),3.53 (d, J = 14.1 Hz, 2 H, CH 2 -Ph), 3.36 (d, J = 14.1 Hz, 2 H, -CH 2 -Ph),1.47 (d, J = 6.9 Hz, 3 H, -CH 3 ).13 C NMR (151 MHz, CDCl 3 ): delta = 140.9 (2¡ÁC, Cq Ph ), 128.6 (4¡ÁC, -Ph),128.2 (4¡ÁC, -Ph), 126.7 (2¡ÁC, -Ph), 88.9 (Cq Fc ), 69.1 (-CH Fc ), 68.7 (5¡ÁC,Cp Fc ), 67.6 (-CH Fc ), 67.1 (-CH Fc ), 66.9 (-CH Fc ), 52.3 (2¡ÁC, -CH 2 -Ph), 52.2(-CH alpha ), 15.4 (-CH 3 ).HRMS (ESI): m/z calcd for [M + H + ] C 26 H 28 FeN + : 410.1571; found:410.1565.
The synthetic route of 1271-51-8 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Plevova, Kristina; Mudrakova, Brigita; ?ebesta, Radovan; Synthesis; vol. 50; 4; (2018); p. 760 – 763;,
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