1036
J. S. Yadav et al. / Tetrahedron Letters 49 (2008) 1034–1036
ammonium chloride (10 mL) and extracted with ethyl acetate
(3 Â 10 mL). The combined organic extracts were dried over anhy-
drous Na2SO4 and concentrated in vacuo. The resulting product was
purified by column chromatography on silica gel (Merck, 100–200
mesh, ethyl acetate–hexane, 1:7) to afford the pure product. Product
3k has been reported in the literature.20 Spectral data for selected
products: 4-Phenyl-1,7-octadien-4-ol (3a): Liquid, IR (KBr): m 3449,
metathesis and dehydration), which are important building
blocks in organic synthesis.
Acknowledgment
S.K.B., S.S. and P.V.M. thank the CSIR, New Delhi,
for the award of fellowships.
3063, 2926, 2852, 2365, 1719, 1631, 1461, 1281, 907, 811, 739 cmÀ1
;
1H NMR (300 MHz, CDCl3): d 8.08–7.81 (m, 2H), 7.33–7.11 (m, 3H),
5.92–5.72 (m, 2H), 5.17–5.09 (m, 4H), 2.39 (dd, 2H, J = 6.3, 13.9 Hz),
2.02–1.64 (m, 4H); 13C NMR (75 MHz, Proton decoupled CDCl3): d
30.1, 39.4, 51.3, 74.4, 116.1, 118.3, 128.2, 129.4, 135.1, 137.2, 138.8,
149.1; LC-MSD-Trap-SL: m/z: 225 (M+23); HRMS calcd for
C14H18O: 202.1357; found, 202.1367. 4-(4-Methoxyphenyl)-1,7-oct-
adiene-4-ol (3c): Liquid, IR (KBr): m 3448, 2924, 2855, 2365, 1732,
References and notes
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564.
5. Miranda, P. O.; Dıaz, D. D.; Padron, J. I.; Bermejo, J.; Martın, V. S.
Org. Lett. 2003, 5, 1979–1982.
6. Miranda, P. O.; Ramırez, M. A.; Padron, J. I.; Martın, V. S.
Tetrahedron Lett. 2006, 47, 283–286.
7. Yadav, J. S.; Reddy, B. V. S.; Narayana Kumar, G. G. K. S.; Swamy,
T. Tetrahedron Lett. 2007, 48, 2205–2208.
8. Yadav, J. S.; Reddy, B. V. Subba; Mahesh Kumar, G.; Murty, Ch. V.
S. R. Tetrahedron Lett. 2001, 42, 89–91.
1642, 1513, 1458, 1364, 1249, 1177, 1037, 916, 826 cmÀ1 1H NMR
;
(200 MHz, CDCl3): d 7.07 (dd, J = 8.0, 15.4 Hz, 2H), 6.75 (d,
J = 8.8 Hz, 2H), 5.98–5.77 (m, 2H), 5.16–4.97 (m, 4H), 3.78 (s, 3H),
2.86 (s, 2H), 2.17 (d, J = 7.3 Hz, 4H); 13C NMR (75 MHz, Proton
decoupled, CDCl3): d 36.1, 39.4, 43.3, 55.1, 73.9, 113.5, 113.8, 118.6,
129.2, 131.5, 134.9, 137.1, 158.2; LC-MSD-Trap-SL: m/z: 255
(M+23). HRMS calcd for [M+Na] C15H20O2Na: 255.1360; found,
255.1363. 4-(4-Methylphenyl)-1,7-octadiene-4-ol (3e): Liquid, IR
(KBr): m 3444, 3067, 2925, 2855, 2364, 1724, 1638, 1457, 1283, 912,
813, 759, 539 cmÀ1 1H NMR (300 MHz, CDCl3): d 7.07–6.97 (m,
;
9. Yadav, J. S.; Subba Reddy, B. V.; Maity, T.; Narayana Kumar, G. G.
K. S. Tetrahedron Lett. 2007, 48, 7155–7159.
10. Shen, K.-H.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2007, 48,
6348–6351.
11. Sabitha, G.; Reddy, Ch. S.; Babu, R. S.; Yadav, J. S. Synlett 2002,
366.
12. Phil, H. L. Bull. Korean Chem. Soc. 2007, 28, 17–28.
13. Podlech, J.; Maier, T. C. Synthesis 2003, 633–655.
14. Ranu, B. C. Eur. J. Org. Chem. 2000, 2347–2356.
15. Yadav, J. S.; Reddy, B. V. S.; Reddy, K. S.; Reddy, K. B. Tetrahedron
Lett. 2002, 43, 1549–1551.
16. Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett.
2001, 42, 6385–6388.
17. Yadav, J. S.; Anjaneyulu, S.; Moinuddin Ahmed, Md.; Reddy, B. V.
S. Tetrahedron Lett. 2001, 42, 2557–2559.
4H), 5.80–5.50 (m, 2H), 5.09–4.82 (m, 4H), 2.76–2.37 (m, 3H), 2.31 (s,
3H), 2.18–1.85 (m, 3H); 13C NMR (75 MHz, Proton decoupled,
CDCl3): d 21.0, 29.6, 36.0, 39.5, 51.4, 74.1, 115.8, 118.2, 128.3, 129.1,
134.9, 137.0, 138.6; LC-MSD-Trap-SL: m/z: 239 (M+23); HRMS
calcd for C15H20O: 216.1514; found, 216.1521. 4-(4-Methylphenyl)-
1,7-octadiyn-4-ol (3f): Liquid, IR (KBr): m 3485, 2961, 2892, 1371,
791 cmÀ1 1H NMR (200 MHz, CDCl3): d 7.36 (d, 2H, J = 8.3 Hz),
;
7.14 (d, 2H, J = 8.3 Hz), 2.88 (d, 2H, J = 2.3 Hz), 2.63 (br, 1H), 2.36
(s, 3 H), 2.23 (d, 1H, J = 2.3 Hz), 2.09 (m, 2H), 2.01 (d, 1H,
J = 2.3 Hz), 1.92 (m, 2H); 13C NMR (75 MHz, Proton decoupled
CDCl3): d 15.1, 21.2, 32.9, 39.8, 68.6, 78.5, 80.2, 84.7, 84.9, 128.3,
129.2, 137.0, 141.2. LC-MSD-Trap-SL: m/z (%): 235 (M+23), 174,
141, 129, 102, 74; HRMS calcd for [M+Na] C15H16ONa: 235.1098;
found, 235.1107. 1-Bromo-2-(4-nitrophenyl)-4-penten-2-ol (3l):
Liquid, IR (KBr): m 3549, 2868, 1521, 1350, 1495, 1445, 1329, 1261,
956, 712 cmÀ1 1H NMR (200 MHz, CDCl3): d 8.23 (d, J = 8.7 Hz,
;
18. Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Synlett 2001, 1608–
1610.
2H), 8.09 (d, J = 8.7 Hz, 2H), 5.76–5.65 (m, 1H), 5.08 (m, 2H), 3.96
(dd, 2H, J = 3.2, 10.9 Hz), 2.56 (s, 2H), 2.26 (br, 1H); 13C NMR (75
MHz, Proton decoupled, CDCl3): d 43.2, 49.7, 74.5, 115.8, 119.8,
129.3, 135.9, 145.3, 158.1 HRMS calcd for [M+Na] C11H12
BrNO3Na: 307.9898; found, 307.9905.
19. General procedure: A mixture of allylbromide/propargyl bromide
(2.5 mmol) and indium metal (2.6 mmol) was stirred in THF at room
temperature for 15–20 min to dissolve the metal then phenacyl
bromide (1 mmol) was added and the reaction stirred for the
appropriate time (Table 1). After complete conversion as indicated
by TLC, the reaction mixture was quenched with aqueous saturated
20. Yadav, J. S.; Reddy, B. V. S.; Vishnumuthy, P.; Biswas, S. K.
Tetrahedron Lett. 2007, 48, 6641–6643.