1304
J. S. Yadav et al.
PAPER
13C NMR (75 MHz, CDCl3): d = 55.3, 105.8, 119.0, 120.3, 123.4,
123.6, 124.2, 125.0, 125.9, 126.4, 126.6, 127.3, 128.0, 128.9, 129.7,
129.8, 130.0, 132.9, 134.6, 150.4, 153.3, 157.9, 158.1.
IR (KBr): 3445, 3047, 2924, 2361, 1744, 1586, 1490, 1439, 1349,
1269, 1159, 1122, 1071, 1022, 941, 854, 817, 778, 743, 682, 630,
530, 474, 419 cm–1.
ESI-MS: m/z = 349 [M + Na]+, 333, 386.
1H NMR (200 MHz, CDCl3): d = 7.93–7.88 (m, 1 H), 7.81–7.73 (m,
3 H), 7.53–7.40 (m, 3 H), 7.32–7.24 (m, 4 H), 6.59 (s, 1 H), 6.57 (s,
1 H), 1.37 (br, 1 H).
2-[1-(6-Methoxy-2-naphthyl)vinyl]-1-naphthol (3h)
Liquid.
13C NMR (75 MHz, CDCl3): d = 123.1, 125.6, 125.7, 126.0, 126.2,
126.7, 127.3, 127.6, 127.7, 128.2, 128.4, 128.6, 128.9, 132.1, 133.4,
136.4.
IR (KBr): 3490, 3256, 3048, 2922, 1889, 1625, 1596, 1509, 1463,
1404, 1270, 1201, 1170, 1029, 956, 840, 803, 741, 615, 580, 474
cm–1.
1H NMR (200 MHz, CDCl3): d = 8.18 (d, J = 8.7 Hz, 2 H), 7.71–
7.50 (m, 5 H), 7.42–7.25 (m, 4 H), 6.98 (d, J = 2.9 Hz, 1 H), 5.97
(d, J = 1.4 Hz, 1 H), 5.36 (d, J = 1.4 Hz, 1 H), 5.21 (s, 1 H), 3.89 (s,
3 H).
13C NMR (75 MHz, CDCl3): d = 55.3, 105.8, 116.4, 120.0, 120.6,
122.6, 123.6, 123.6, 125.0, 126.8, 126.9, 127.8, 128.6, 129.6, 129.9,
131.5, 131.8, 132.4, 134.8, 136.5, 150.4, 153.4, 158.1.
ESI-MS: m/z = 301 [M + 39]+, 278.
Acknowledgment
S.S. and S.K.B. thank CSIR New Delhi for the award of fel-
lowships.
References
ESI-MS: m/z = 327 [M + 1]+, 276.
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1-(1-Phenylethyl)-2-naphthol (3i)
Liquid.
IR (KBr): 3371, 2922, 2852, 1662, 1459, 1279, 1073, 700 cm–1.
1H NMR (200 MHz, CDCl3): d = 8.00 (d, J = 8.6 Hz, 1 H), 7.75 (d,
J = 7.8 Hz, 1 H), 7.63 (d, J = 9.4 Hz, 1 H), 7.46–7.23 (m, 7 H), 6.97
(d, J = 9.4 Hz, 1 H), 5.15 (q, J = 7.03 Hz, 1 H), 4.75 (br s, 1 H), 1.77
(d, J = 7.03 Hz, 3 H).
13C NMR (75 MHz, CDCl3): d = 17.1, 34.8, 119.3, 122.6, 123.1,
123.8, 126.5, 126.7, 127.1, 128.7, 128.9, 129.0, 129.7, 132.8, 143.7,
151.5.
ESI-MS: m/z = 249 [M + 1]+, 220, 201, 175, 132, 110.
2-(1-Phenylethyl)-1-naphthol (3j)
Liquid.
IR (KBr): 3442, 3025, 2925, 2854, 1712, 1659, 1595, 1491, 1453,
1379, 1301, 1252, 1159, 1026, 900, 761, 699, 554 cm–1.
1H NMR (200 MHz, CDCl3): d = 8.04–8.01 (m, 1 H), 7.87–7.84 (m,
1 H), 7.74–7.69 (m, 2 H), 7.38 (dd, J = 3.7, 3.0 Hz, 1 H), 7.30–7.27
(m, 4 H), 7.24 (t, J = 4.5 Hz, 2 H), 4.97 (s, 1 H), 4.41 (q, J = 7.5 Hz,
1 H), 1.71 (dd, J = 6.5, 1.5 Hz, 3 H).
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J. Am. Chem. Soc. 2001, 123, 11310. (b) Choi, D. S.; Kim,
J. H.; Shin, U. S.; Deshmukh, R. R.; Song, C. E. Chem.
Commun. 2007, 3482. (c) Kido, Y.; Yonehara, F.;
Yamaguchi, M. Tetrahedron 2001, 57, 827.
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ESI-MS: m/z = 271 [M + 23]+, 376, 393.
2-(1-Phenylethyl)phenol (3k)
Liquid.
IR (KBr): 3533, 3060, 3027, 2966, 2926, 2873, 1644, 1599, 1495,
1452, 1373, 1330, 1255, 1207, 1110, 1027, 840, 753, 700, 587, 542
cm–1.
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Int. Ed. 2002, 41, 2138. (b) Viswanathan, G. S.; Li, C.-J.
Synlett 2002, 1553. (c) Viswanathan, G. S.; Li, C.-J.
Tetrahedron Lett. 2002, 43, 1613. (d) Yadav, J. S.; Reddy,
B. V. S.; Eeshwaraiah, B.; Gupta, M.; Biswas, S. K.
Tetrahedron Lett. 2005, 46, 1161.
1H NMR (200 MHz, CDCl3): d = 7.22–7.15 (m, 3 H), 7.06–7.02 (m,
3 H), 6.87 (t, J = 7.3 Hz, 2 H), 6.70–6.58 (m, 1 H), 5.53 (s, 1 H),
4.08 (q, J = 7.3 Hz, 1 H), 1.61 (d, J = 7.3 Hz, 3 H).
ESI-MS: m/z = 199 [M + 1]+, 287, 282.
1-(1-Phenylvinyl)naphthalene-2-thiol (3l)
Solid.
Synthesis 2009, No. 8, 1301–1304 © Thieme Stuttgart · New York