反応 #42706

反応方程式

cinnamyl carbonate

m-anisidine

→

title compound

収率 82.6%

α-Ethynyl-N-(m-methoxyphenyl)-benzenemethanamine

収率 82.6%

反応条件

後処理

1. 1
   その他1H NMR analysis of the crude reaction mixture
2. 2
   その他The mixture was purified by flash column chromatography on silica gel (4% ethyl acetate in hexanes)

実験手順

The general procedure was followed with cinnamyl carbonate (0.188 g, 0.979 mmol) and m-anisidine (0.150 g, 1.22 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 97/3. The mixture was purified by flash column chromatography on silica gel (4% ethyl acetate in hexanes) to give the title compound (0.192 g, 82%). [α]DRT=(c, CHCl3). 1H NMR (400.13 MHz, CDCl3) δ 7.50-7.40 (m, 4H), 7.36 (tt, J=6.8, 2.0 Hz, 1H), 7.14 (t, J=8.0 Hz, 1H), 6.37 (dd, J=8.0, 2.4 Hz, 1H), 6.32 (dd, J=8.4, 2.0 Hz, 1H), 6.12 (ddd, J=16.8, 10.0, 6.0 Hz, 1H), 5.37 (dt, J=16.8, 1.4 Hz, 1H), 5.32 (dt, J=10.4, 1.4 Hz, 1H), 5.03 (br s, 1H), 4.18 (br s, 1H), 3.79 (s, 3H). 13C NMR (100.59 MHz, CDCl3) δ 160.50, 148.47, 141.68, 138.84, 129.71, 128.63, 127.35, 127.02, 115.98, 106.53, 102.62, 99.46, 60.71, 54.85. Anal. Calcd for C16H17NO: C, 80.30; H, 7.16; N, 5.85. Found: C, 80.17; H, 7.24; N, 5.78.

出典