Reaction #2040
ord-2f15776952b34a539da4eb150087740b
Reaction equation
Reactants
Reagents
Solvents
Conditions
Procedure
Starting from 1-butyne and 1-bromo-6-(tetrahydropyran-2-yloxy)-hexane (22), the (3E,11Z)-3,11-tetradecadien-1-yl acetate (30) was prepared by a synthetic route similar to that used for the preparation of (3E,8Z)-3,8-tetradecadien-1-yl acetate (21), as depicted in the following scheme. ##STR18## The yield was 15% [17 mg; 96% isomeric purity (GC)] based on the starting material, 1-bromo-6-(tetrahydropyran-2-yloxy)hexane (22). 1H NMR (500 MHz) δ: 5.51 (dtt, J=15.1, 6.8, 6.8, 1.2, 1.5 Hz, 1H, =CH -3), 5.35 (m, 3H, CH=CH -4, 11, 12), 4.06 (t, J=6.8, 6.8 Hz, 2H, CH2 -1), 2.31 (dddt, J=1.2, 1.2, 6.8, 6.8, 6.8 Hz, 2H, CH2 -2), 2.05 (s, 3H, COCH3), 2.02 (m, 6H, CH2 -5, 10, 13), 1.36-1.24 (m, 6H, CH2 -6, 7, 8, 9), 0.95 (t, J=7.3, 7.6 Hz, 3H, CH3). 13 C NMR (100.6 MHz) δ: 171.1 (C=O), 133.6 (=CH-3), 131.6 (=CH-12), 129.3 (=CH-11), 125.0 (=CH-4), 64.1 (CH2 -1), 32.6 (CH2 -2), 31.9 (CH2 -6), 29.7 (CH2 -8), 29.3 (CH2 -7), 29.1 (CH2 -9), 29.0 (CH2 -10), 27.1 (CH2 -5), 21.0 (COCH3), 20.5 (CH2 -13), 14.4 (CH3 -14). MS [EI, m/z(%)] 192 (M+ -60, 6), 163 (6), 149 (9), 135 (12), 121 (16), 107 (16), 96 (28), 95 (37), 93 (25), 82 (50), 81 (60), 80 (35), 79 (36), 69 (33) 68 (64), 67 (97), 55 (45), 43 (100), 41 (67). IR (CCl4, cm-1) 3006 (=CH cis str), 1743 (C=O), 1238, 1036 (C--O), 969 (=CH trans wag). IR (gas phase, cm-1) 3012 (cis =C--H str), 2934 (CH2), 1761 (C=O), 1231, 1038 (--O--), 968 (=CH trans wag).