Reacción #42705

Ecuación de reacción

cinnamyl carbonate

p-iodoaniline

→

title compound

Rendimiento 92.9%

α-Ethynyl-N-(p-iodophenyl)-benzenemethanamine

Rendimiento 92.9%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro1H NMR analysis of the crude reaction mixture
2. 2
   OtroThe mixture was purified by flash column chromatography on silica gel (1.5% ethyl acetate in hexanes)

Procedimiento

The general procedure was followed with cinnamyl carbonate (0.188 g, 0.979 mmol) and p-iodoaniline (0.220 g, 1.04 mmol). The reaction was conducted at room temperature for 12 h. 1H NMR analysis of the crude reaction mixture indicated the ratio of regioisomers to be 98/2. The mixture was purified by flash column chromatography on silica gel (1.5% ethyl acetate in hexanes) to give the title compound (0.303 g, 92%). HPLC analysis indicated the enantiomeric excess of the product was 96% [Diacel CHIRALCEL OD-H (0.46 cm×25 cm); hexane/2-propanol=99/1; flow rate=0.6 mL/min; detection wavelength=254 nm; TR=18.4 (major), 23.1 (minor) min]: [α]DRT=(c, CHCl3). 1H NMR (400.13 MHz, CDCl3) δ 7.48-7.40 (m, 6H), 7.36 (s, J=4.6 Hz, 1H), 6.43 (dt, J=8.8, 2.4 Hz, 2H), 6.09 (ddd, J=16.8, 10.4, 6.0 Hz, 1H), 5.34 (dt, J=12.0, 1.3 Hz, 1H), 5.31 (dt, J=5.2, 1.2 Hz, 1H), 4.97 (d, J=5.6 Hz, 1H), 4.15 (br s, 1H). 13C NMR (100.59 MHz, CDCl3) δ 146.53, 141.10, 138.35, 137.51, 128.72, 127.53, 126.99, 116.28, 115.69, 78.32, 60.46. Anal. Calcd for C15H14NI: C, 53.75; H, 4.21; N, 4.18; I, 37.86. Found: C, 53.59; H, 4.27; N, 4.17; I, 38.04.

Fuente