反応 #1183909

反応方程式

1-naphthalen-1-yl-hex-5-en-1-yn-3-ol

→

desired compound

収率 57.0%

1-naphthalen-1-yl-bicyclo[3.1.0]hexan-3-one

収率 57.0%

溶媒

toluene

反応条件

後処理

1. 1
   濃縮The organics were concentrated in vacuo
2. 2
   その他to afford a black residue
3. 3
   その他The crude material was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 10%:90%)

実験手順

To a stirred solution of 1-naphthalen-1-yl-hex-5-en-1-yn-3-ol (1.00 g, 4.50 mmol) under an atmosphere of nitrogen in toluene (100 mL) was added platinum chloride (0.06 g, 0.22 mmol, 5 mol %); the resulting black mixture was stirred at 80° C. for 24 hr. TLC indicated that the reaction was complete. The organics were concentrated in vacuo to afford a black residue. The crude material was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 10%:90%) to afford the desired compound as a yellow oil (0.57 g, 57%). 1H NMR (400 MHz, CDCl3) δ ppm 0.73 (1H, t, J 4.0 Hz, CH), 0.82-0.84 (1H, m, CH), 1.17-1.24 (1H, m, CH), 2.47 (1H, d, J 19.0 Hz, CH), 2.75 (2H, d, J 10 Hz, CH)), 2.95-3.09 (1H, m, CH), 7.38-7.51 (4H, m, ArH), 7.73 (1H, d, J 8.0 Hz, ArH), 7.84 (1H, d, J 8.0 Hz, ArH), 8.10 (1H, d, J 8.0 Hz, ArH).

出典