تفاعل #2038
ord-e5f31ed3fd4346d9967feec4d8f3e24d
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1-(Tetrahydropyran-2-yloxy)-4-decyne (15) (0.5 g, 2.1 mmol), prepared according to Example 13, was hydrogenated in ethanol (20 ml) over P2-Ni, formed from nickel acetate (75 mg) deactivated with ethylenediamine (0.2 ml) for 4 hr. After chromatography on silica gel, the product (16) (0.43 g) was obtained in 85% yield. GC (Rt): starting material 15, 22.18 min, 0.4%; desired product 16 21.59 min, 97.9%; the 4E isomer of 16, 21.75 min, 1.7%. 1H NMR (200 MHz ) δ: 5.37 (m, 2H, CH=CH-4, 5), 4.58 (m, 1H, CH-2'), 3.60 (m, 4H, CH2 -1, 6'); 2.12 (M, 2H, CH2 -6); 2.04 (m, 2H, CH2 -3); 1.16 (tt, 2H, J=6.8, 6.8, 7.0, 7.0 Hz, CH2 -2), 1.4-1.9 (m, 6H, CH2 -3', 4', 5'), 1.29 (m, 6H, CH2 -7, 8, 9); 0.88 (t, 3H, J=7.0 Hz, CH3). IR (CCl4, cm-1) 3007, 1653, 1201, 1138, 1120 1034. MS [FAB, m/z(%)] 239 (M+ -1), 85 (100).