4
Tetrahedron
18. Alonso, E.; Ramón, D.J.; Yus, M. J. Org. Chem. 1997, 62, 417-
C5´). MS (EI, 70 eV) m/z (rel. int.): [M+] 270 (100), 269 (23),
239 (10), 224 (10), 212 (9), 196 (12), 195 (10), 181 (10), 165 (10),
152 (15), 144 (8), 141 (10), 115 (10). HRMS-DART calculated for
C17H19O3 [M+H+] 271.13342, found: 271.13268
421.
19. Solladié, G.; Paturel-Jacopé; Maignan, J. Tetrahedron 2003, 59,
3315-3321.
20. Robinson, J. E.; Taylor, R. J. K. Chem. Commun. 2007, 1617-
1619.
21. Hilt, G.; Hengst, C. J.Org. Chem. 2007, 72, 7337-7342.
22. Lara-Ochoa, F.; Espinosa-Pérez, G. Tetrahedron Lett., 2007, 48,
7007-7010.
27. (E)-3´,4,5´-trimethoxy-stilbene (6), IR (KBr) cm-1: 2834.1, 1587.5,
1509.4, 1455.5, 1424.4, 1249.2, 1147.7, 958.5, 827.3, 1H RMN
(CDCl3) d ppm: 3.82 (s, 9H, 3 CH3), 6.37 (t, 1H, H4´), 6.65 (d,
2H, H2´, H6´), 6.89 (dt, 2H, H3, H5), 6.905 (d, J=16.2 Hz,
CH=CH), 7.03 (d, J=16.25 Hz, CH=CH), 7.44 (dt, 2H, H2, H6).
13C RMN (CDCl3) d ppm: 55.389 (3 OCH3), 99.623 (C4´),
104.358 (C2´, C6´), 114.152 (C3, C5), 126.564 (CH=CH),
127.794 (C2, C6), 128.731 (CH=CH), 129.921 (C1), 139.689
(C1´), 159.391 (C4), 160.959 (C3´, C5´). MS (EI, 70 eV) m/z (rel.
int.): [M+] 270 (100), 269 (25), 239 (8), 224 (10), 212 (10), 196
(10), 195 (9), 181 (8), 165 (10), 152 (15), 141 (10), 115 (10).
HRMS-DART calculated for C17H19O3 [M+H+] 271.13342, found:
271.13329.
23. Magoon, E. F.; Slaugh, L. H. Tetrahedron 1967, 23 (12), 4509-
4515.
24. Gabriele, B.; Benabdelkamel, H.; Plastina, P.; Fazio, A.; Sindona,
G.; Di-Donna, L. Synthesis 2008, 18, 2953-2956.
25. 1,3-dimethoxy-5-(4-methoxy-phenylethynyl)-benzene (4), IR
(KBr) cm-1: 2936.2, 2837.5, 2208.6, 1585.5, 1509.5, 1454.7,
1418.6, 1245.8, 1153.5.1H RMN (CDCl3) d ppm: 3.8 (s, 6H, 2
CH3), 3.82 (s, 3H, CH3), 6.44 (t, 1H, H4´), 6.67 (d, 2H, H2´, H6´),
6.87 (dt, 2H, H3, H5), 7.46 (dt, 2H, H2, H6). 13C RMN (CDCl3) d
ppm: 55.277 (OCH3), 55.408 (2 OCH3), 88.042 (C≡C), 88.951
(C≡C), 101.507 (C4´), 109.154 (C2´, C6´), 113.979 (C3, C5),
115.122 (C2, C6), 124.834 (C1), 133.102 (C1´), 159.645 (C4),
160.478 (C3´, C5´). MS (EI, 70 eV) m/z (rel. int.): [M+] 268
(100), 253 (18), 225 (10), 210 (6), 195 (4), 182 (4), 152 (10), 134
(10). HRMS-DART calculated for C17H17O3 [M+H+] 269.11777,
found: 269.11689
28. (E)-3´,4,5´-trihydroxy-stilbene (1), IR (KBr) cm-1:3299.0, 1585.5,
1383.5, 1147.7. 1H RMN (Metanol-d4) d ppm: 6.18 (t, 1H, H4´),
6.46 (d, 2H, H2´, H6´), 6.76 (dt, 2H, H3, H5), 6.79 (d, J=16.2 Hz,
CH=CH), 6.95 (d, J=16.25 Hz, (CH=CH), 7.34(dt, 2H, H2, H6).
13C RMN (CDCl3) d ppm: 102.640 (C4´), 105.779 (C2´, C6´),
116.473 (C3, C5), 126.946 (CH=CH), 128.757 (C2, C6), 129.379
(CH=CH), 130.354 (C1), 141.269(C1´), 158.280 (C4), 159.545
(C3´, C5´). MS (EI, 70 eV) m/z (rel. int.): [M+] 228 (100), 227
(13), 211 (8), 181 (18), 165 (8), 152 (8), 144 (5), 141 (5), 128 (5),
115 (8), 114 (5). HRMS-DART calculated for C14H13O3 [M+H+]
229.08647, found: 229.08662
26.
A sample of the mixture (5) was purified by column
chromatography and spectral data of the Z isomer are the
following: IR (KBr) cm-1: 2834.3, 1588.7, 1508.9, 1455.9, 1425.5,
1248.1, 1203.6, 1153.8, 862.3, 835.0.1H RMN (CDCl3) d ppm:
3.77 (s, 9H, 3 CH3), 6.31 (t, 1H, H4´), 6.43 (d, 2H, H2´, H6´), 6.45
(d, J=12.3 Hz, CH=CH), 6.52 (d, J=12.33 Hz, CH=CH), 6.76 (dt,
2H, H3, H5), 7.21 (dt, 2H, H2, H6).13C RMN (CDCl3) d ppm:
55.205 (3 OCH3), 99.623 (C4´), 106.606 (C2´, C6´), 113.516 (C3,
C5), 126.667 (CH=CH), 129.549 (C1), 130.140 (CH=CH),
130.263 (C2, C6), 139.471 (C1´), 158.731 (C4), 160.556 (C3´,
Highlights
It has been developed a synthesis of resveratrol
with good yields and high purity
Resveratrol has been synthesized by an effective
and simple reaction
Was produced in 4-step including a simple
Sonogashira type reaction with 93 % yields