反应详情

To a flask equipped with magnetic stirred condenser and drying tube filled with calcium chloride, 3.0 g, (13.95 mmol) of piperonyl bromide, 2.0 g (27.9 mmol) of 2-butyn-1-ol and 50 ml of dichloroethane are placed. After the addition of zinc(II) oxide (1.1 g, 13.5 mmol) the suspension is stirred at room temperature for 1 hour. The reaction is accompanied by a characteristic chance of colour. The mixture is then filtered, the filtrate is evaporated. The residual oil is dissolved in 50 ml of ether, washed within 2×10 ml of water, dried and evaporated. Yield 2.3 g (11.2 mmol, 80.7%), GC 82%. IR(CHCl3, cm−1) υ: 2997, 2946, 2921, 2888, 2376, 1609, 1503, 1491, 1445, 1251, 1099, 1070, 1042, 937, 865, 810; 1H-NMR (400 MHz, CDCl3) δ: 1.87 (3H, t, J=2.3 Hz, Me), 4.10 (2H, q, J=2.3 Hz, O—CH2—C≡), 4.47, (2H, s, O—CH2—Ar), 5.94 (2H, s, O—CH2—O), 6.76 (1H, d, J=8 Hz, H-7), 6.81 (1H, dd, J=8.15 Hz, H-6), 6.86 (1H, J=1.5 Hz, H-4); 13C-NMR (100 MHz, CDCl3) δ: 3.52 (Me), 57.29 (O—CH2—C≡), 71.15 (O—CH2—Ar), 82.54 (CH3—C≡), 100.9 C-2, 107.95, 108.71 (C-4, 7), 121.66 (C-6), 131.39, (C-5), 147.15, 147.66 (C3a, C-7a);

1. customTo a flask equipped with magnetic stirred condenser
2. customdrying tube
3. filtrationThe mixture is then filtered
4. customthe filtrate is evaporated
5. dissolutionThe residual oil is dissolved in 50 ml of ether
6. washwashed within 2×10 ml of water
7. customdried
8. customevaporated