Y. Nishimoto et al. / Tetrahedron 65 (2009) 5462–5471
5471
was added 4-methoxybenzyl chloride (1.0 mmol) at 0 ꢀC. The
mixture was stirred and warmed to room temperature for 2 h.
Then, 1-phenyl-1-trimethylsiloxyethene (2 mmol) was added to
the reaction mixture and the mixture was stirred at room tem-
perature for 2 h. The reaction was quenched by H2Oaq, and the
mixture was extracted with diethyl ether. The collected organic
layer was dried (MgSO4). The solvent was evaporated and the
mixture of the crude product, 1 N HClaq (1.5 mL), and THF (10 mL)
was stirred at 0 ꢀC for 1 h. Then, the reaction was quenched by
NaHCO3aq. The mixture was extracted with diethyl ether. The
collected organic layer was dried (MgSO4). The solvent was evap-
orated and the residue was purified by column chromatography
(hexane/ethyl acetate¼70/30, column length 11 cm) to give the
product. Mp 112–113 ꢀC. IR: (KBr) 3518 (OH), 1670 (C¼O) cmꢁ1; 1H
NMR: (400 MHz, CDCl3) 7.94 (d, J¼7.2 Hz, 2H, 1-Ph-o), 7.56 (t,
J¼7.2 Hz, 1H, 1-Ph-p), 7.45 (t, J¼7.2 Hz, 2H, 1-Ph-m), 7.13 (d,
J¼8.8 Hz, 2H, 5-Ph-o), 6.82 (d, J¼8.8 Hz, 2H, 5-Ph-m), 3.94 (ddd,
J¼10.0, 3.2, 1.6 Hz, 1H, 3-H), 3.77 (s, 3H, OMe), 3.38 (d, J¼3.2 Hz, 1H,
OH), 3.20 (dd, J¼17.2, 1.6 Hz, 1H, 2-HA), 3.03 (dd, J¼17.2, 10.0 Hz, 1H,
2-HB), 2.82 (d, J¼13.2 Hz, 1H, 5-HA), 2.51 (d, J¼13.2 Hz, 1H, 5-HB),
0.97 (s, 3H, 4-MeA), 0.87 (s, 3H, 4-MeB); 13C NMR: (100 MHz, CDCl3)
201.6 (s, C-1), 157.8 (s, 5-Ph-p), 136.4 (s, 1-Ph-i), 133.4 (d, 1-Ph-p),
131.6 (d, 5-Ph-o), 130.6 (s, 5-Ph-i), 128.6 (d, 1-Ph-m), 127.9 (d, 1-Ph-
o), 113.1 (d, 5-Ph-m), 72.8 (d, C-3), 55.1 (q, OMe), 43.6 (t, C-5), 39.6
(t, C-2), 37.9 (s, C-4), 23.3 (q, 4-MeB), 22.2 (q, 4-MeA); MS: (EI, 70 eV)
m/z 312 (Mþ, 1.4), 121 (MeOC6H4CH2, 100), 105 (24); HRMS: (EI,
70 eV) calculated (C20H24O3) 312.1725 (Mþ), found: 312.1727.
7. Chlorination of alcohol: Yasuda, M.; Shimizu, K.; Yamasaki, S.; Baba, A. Org.
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5.3.16. Methyl 2,2-dimethyl-3-phenyl-4-pentenoate 26
IR: (deposit from CDCl3) 1736 (C]O) cmꢁ1; 1H NMR: (400 MHz,
CDCl3) 7.28 (t, J¼7.0 Hz, 2H, m), 7.22 (t, J¼7.0 Hz, 1H, p), 7.17 (d,
J¼7.0, 2H, o), 6.23 (ddd, J¼16.0, 12.0, 8.0 Hz, 1H, 4-H), 5.14–5.12 (m,
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46.9 (s, C-2), 23.2 (q, 2-MeA), 22.2 (q, 2-MeB); MS: (EI, 70 eV) m/z
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Acknowledgements
This work was supported by Grant-in-Aid for Scientific Research
on Priority Areas (No. 18065015, ‘Chemistry of Concerto Catalysis’
and No. 20036036, ‘Synergistic Effects for Creation of Functional
Molecules’) and for Scientific Research (No. 19550038) from Min-
istry of Education, Culture, Sports, Science and Technology, Japan.
Y.N. thanks The Global COE Program ‘Global Education and Re-
search Center for Bio-Environment Chemistry’ of Osaka University.
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