Tributylvinyltin → Benzene, 4-ethenyl-2-nitro-1-(phenylmethoxy)-

Participants

Reaction Steps

A mixture of Example 68A (2.18 g, 7.08 mmol), Pd(PPh3)4 (1.23 g, 1.06 mmol) and tributyl-vinyl-stannane (2.48 mL, 8.49 mmol) in DMF (200 mL) was heated at 80° C. overnight. The solvent was removed by vacuum pump. The residue was dissolved in acetone (50 mL), and dried with silica gel powder (20 g). 10% ethyl acetate in hexanes (2 L) was used to run flash chromatography to give the title compound (1.69 g, 94%). MS (DCI) m/z 273.03 (M+NH4)+; 1H NMR (500 MHz, CD2Cl2) δ ppm 5.23 (s, 2 H) 5.72 (d, J=17.47 Hz, 1 H) 6.67 (dd, J=17.78, 10.92 Hz, 1 H) 7.12 (d, J=8.73 Hz, 1 H) 7.35 (m, 1 H) 7.38–7.43 (m, 2 H) 7.44–7.48 (m, 2 H) 7.56 (dd, J=8.73, 2.18 Hz, 1 H) 7.87 (d, J=2.18 Hz, 1 H).

Provenance & Evidence