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K. Takai et al. / Tetrahedron 62 (2006) 7534–7539
1H); 13C NMR (CDCl3): d 14.1, 22.7, 26.07, 26.15, 26.6,
28.7, 28.8, 29.16, 29.23, 29.3, 29.5, 29.60, 29.61, 31.9,
32.3, 43.7, 77.7, 131.4, 133.1. Anal. Calcd for C19H36O:
C, 81.36; H, 12.94. Found: C, 81.20; H, 13.12.
969, 747 cmꢂ1; H NMR (CDCl3): d 1.20–1.31 (m, 12H),
1.43–1.58 (m, 3H), 2.13 (s, 3H), 2.36 (dt, J¼7.7, 7.8 Hz,
2H), 2.41 (t, J¼7.5 Hz, 2H), 2.70 (dd, J¼8.1, 7.2 Hz, 2H),
4.01 (dt, J¼6.6, 6.6 Hz, 1H), 5.46 (dd, J¼15.3, 6.9 Hz,
1H), 5.66 (dt, J¼15.3, 6.6 Hz, 1H), 7.16–7.29 (m, 5H); 13C
NMR (CDCl3): d 23.8, 25.3, 29.1, 29.30, 29.35, 29.4, 29.8,
33.9, 35.6, 37.2, 43.8, 73.0, 125.8, 128.3, 128.4, 130.9,
133.9, 141.7, 209.3. Elemental analysis was conducted
with a trimethylsilyl ether of (E)-11-hydroxy-15-phenyl-
12-pentadecen-2-one [bp 150 ꢀC (bath temp, 0.3 Torr)].
Anal. Calcd for C24H40O2Si: C, 74.17; H, 10.37. Found: C,
74.29; H, 10.42.
1
3.3.7. 2-Phenyl-1-undecen-3-ol.23 IR (neat): 3415, 3080,
3056, 2924, 2854, 1630, 1574, 1494, 1465, 1378, 1131,
1064, 1027, 908, 777, 698 cmꢂ1; 1H NMR (CDCl3): d 0.87
(t, J¼6.9 Hz, 3H), 1.19–1.28 (m, 11H), 1.42–1.63 (m, 3H),
1.75 (s, 1H), 4.60–4.64 (m, 1H), 5.30 (s, 1H), 5.35 (s, 1H),
7.30–7.40 (m, 5H); 13C NMR (CDCl3): d 14.1, 22.6, 25.6,
29.2, 29.4, 29.5, 31.8, 36.0, 73.9, 112.5, 126.9, 127.5,
128.3, 140.1, 152.2.
3.3.13. 2-Methyleneindan-2-ol. IR (nujol): 3306, 3072,
1662, 1610, 1586, 1317, 1250, 1204, 1174, 1037, 895,
3.3.8. (E)-1-Phenyl-1-undecen-3-ol.24 IR (neat): 3347,
3103, 3082, 3026, 2926, 2855, 1599, 1494, 1465, 965, 748,
1
746 cmꢂ1; H NMR (CDCl3): d 1.81 (d, J¼9.0 Hz, 1H),
1
693 cmꢂ1; H NMR (CDCl3): d 0.88 (t, J¼6.6 Hz, 3H),
3.62 (d, J¼20.0 Hz, 1H), 3.70 (d, J¼20.1 Hz, 1H), 5.29
(dd, J¼4.1, 1.9 Hz, 1H), 5.49 (d, J¼9.0 Hz, 1H), 5.50 (dd,
J¼4.1, 2.1 Hz, 1H), 7.24–7.51 (m, 4H); 13C NMR
(CDCl3): d 36.5, 76.5, 110.4, 124.7, 124.9, 127.1, 128.6,
140.8, 144.0, 152.8; EI MS m/z (%): 146 (M+, 100), 145
(61), 131 (66), 118 (28), 115 (47), 91 (25). HRMS (EI) m/z
calcd for (M+) C10H10O 146.0732, found 146.0732.
1.23–1.45 (m, 12H), 1.55–1.71 (m, 3H), 4.27 (dd, J¼6.6,
6.3 Hz, 1H), 6.21 (dd, J¼15.9, 6.6 Hz, 1H), 6.56 (d,
J¼15.9 Hz, 1H), 7.21–7.38 (m, 5H); 13C NMR (CDCl3):
d 14.1, 22.6, 25.4, 29.2, 29.5, 29.6, 31.8, 37.4, 73.1, 126.4,
127.6, 128.5, 130.1, 132.6, 136.8.
3.3.9. (E)-2-Pentyl-1-phenyl-2-octen-1-ol (7).16 IR (neat):
3357, 3089, 3062, 2955, 2927, 2857, 1493, 1455, 1378,
Acknowledgements
1
1084, 1008, 700 cmꢂ1; H NMR (CDCl3): d 0.83 (t, J¼
6.9 Hz, 3H), 0.90 (t, J¼6.9 Hz, 3H), 1.14–1.15 (m, 12H),
1.77 (d, J¼3.3 Hz, 1H), 1.77–1.86 (m, 1H), 1.93–2.03 (m,
1H), 2.07 (dt, J¼7.3, 7.2 Hz, 2H), 5.16 (d, J¼2.7 Hz, 1H),
5.61 (t, J¼7.2 Hz, 1H), 7.24–7.37 (m, 5H); 13C NMR
(CDCl3): d 14.0, 14.1, 22.4, 22.6, 27.6, 27.7, 29.2, 29.5,
31.7, 32.1, 78.2, 126.5, 127.3, 127.3, 128.2, 141.2, 142.8.
This work was supported by a Grant-in-Aid for Scientific
Research on Priority Areas from the Ministry of Education,
Culture, Sports, Science, and Technology of Japan and by
the Nagase Science and Technology Foundation.
References and notes
3.3.10. 3-Methylene-6-phenyl-hexane-1,4-diol (8). IR
(neat): 3353, 3085, 3026, 2927, 2862, 1645, 1603, 1496,
1. (a) Saito, S. Modern Organonickel Chemistry; Tamaru, Y., Ed.;
Wiley-VCH: Weinheim, 2005; pp 171–204; (b) Reppe, W.;
Schweckendiek, W. J. Justus Liebigs Ann. Chem. 1948, 560,
104–116; (c) Alphonse, P.; Moyen, F.; Mazerolles, P.
J. Organomet. Chem. 1988, 345, 209–216.
2. Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268–
5270.
3. (a) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto,
K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048–6050; (b)
Jin, H.; Uenishi, J.-i.; Christ, W. J.; Kishi, Y. J. Am. Chem.
Soc. 1986, 108, 5644–5646.
1
1454, 1320, 1045, 908, 750, 700 cmꢂ1; H NMR (CDCl3):
d 1.84–1.98 (m, 2H), 2.29–2.33 (m, 2H), 2.43 (ddd,
J¼14.0, 8.1, 6.0 Hz, 1H), 2.64 (ddd, J¼13.8, 9.1, 6.8 Hz,
1H), 2.74 (ddd, J¼13.9, 9.4, 6.4 Hz, 2H), 3.72 (ddd,
J¼10.4, 8.0, 4.7 Hz, 1H), 3.82 (dt, J¼10.5, 5.4 Hz, 1H),
4.13 (t, J¼5.4 Hz, 1H), 4.98 (d, J¼1.2 Hz, 1H), 5.12 (s,
1H), 7.17–7.31 (m, 5H); 13C NMR (CDCl3): d 32.0, 34.8,
37.1, 62.4, 74.9, 113.7, 125.9, 128.41, 128.43, 141.8, 148.8.
Elemental analysis was conducted with a trimethylsilyl ether
of 8 [bp 60 ꢀC (bath temp, 1.3 Torr)]. Anal. Calcd for
C19H34O2Si2: C, 65.08; H, 9.77. Found: C, 65.04; H, 9.85.
4. Hodgson, D. M.; Wells, C. Tetrahedron Lett. 1994, 35, 1601–
1604.
3.3.11. 11-Hydroxy-12-(2-phenylethyl)-12-tridecen-2-
one (9). IR (neat): 3428, 3063, 3027, 2929, 2855, 1713,
5. For transmetallation from zirconium to chromium, see:
Takahashi, T.; Liu, Y.; Chaki, S.; Nakajima, K.; Kanno, K.-i.
J. Am. Chem. Soc. 2005, 127, 11928–11929.
1646, 1604, 1496, 1454, 1360, 1167, 900, 748, 700 cmꢂ1
;
1H NMR (CDCl3): d 1.24–1.28 (m, 12H), 1.51–1.58 (m,
3H), 2.13 (s, 3H), 2.29 (dt, J¼15.3, 7.9 Hz, 1H), 2.41 (t,
J¼7.3 Hz, 2H), 2.42 (dt, J¼15.3, 8.0 Hz, 1H), 2.80 (t,
J¼8.2 Hz, 2H), 4.05–4.09 (m, 1H), 4.92 (d, J¼1.2 Hz,
1H), 5.07 (s, 1H), 7.17–7.31 (m, 5H); 13C NMR (CDCl3):
d 23.8, 25.7, 29.1, 29.3, 29.4, 29.5, 29.8, 32.9, 34.5, 35.5,
43.8, 75.6, 109.9, 125.9, 128.3, 128.3, 142.0, 151.5, 209.3.
Elemental analysis was conducted with a trimethylsilyl ether
of 9 [bp 155 ꢀC (bath temp, 0.34 Torr)]. Anal. Calcd for
C24H40O2Si: C, 74.17; H, 10.37. Found: C, 74.06; H, 10.56.
6. There is a possibility of hydrolysis with a trace amount of water
in the reaction mixture.
7. (a) Hanson, J. R.; Premuzic, E. Angew. Chem., Int. Ed. Engl.
1968, 7, 247–252; (b) Espenson, J. H. Acc. Chem. Res. 1992,
25, 222–227; (c) Wessjohann, L. A. Synthesis 1999, 1–36.
8. Kauffmann, T.; Abeln, R.; Wingbermuhle, D. Angew. Chem.,
Int. Ed. Engl. 1984, 23, 729–730.
¨
9. Takai, K.; Toratsu, C. J. Org. Chem. 1998, 63, 6450–6451; See
also a review on water-accelerated organic transformations:
Ribe, S.; Wipf, P. Chem. Commun. 2001, 299–307.
10. Takai, K.; Sakamoto, S.; Isshiki, T. Org. Lett. 2003, 5, 653–655.
11. For representative examples using hydrozirconation, see:
(a) Maeta, H.; Hashimoto, T.; Hasegawa, T.; Suzuki, K.
3.3.12. (E)-11-Hydroxy-15-phenyl-12-pentadecen-2-one.
IR (neat): 3409, 3026, 2928, 2854, 1715, 1496, 1454, 1361,