The Journal of Organic Chemistry
Page 16 of 31
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H), 6.86 (d, J = 8.6 Hz, 2 H), 5.35ꢀ5.33 (m, 2 H), 4.49 (ab, Jab = 11.6 Hz, 2 H), 3.80 s, 3 H),
3.28ꢀ3.23 (m, 1 H), 2.42ꢀ2.38 (m, 1 H), 2.29ꢀ2.23 (m, 1 H), 2.04ꢀ1.79 (m, 5 H), 1.60ꢀ0.94 (m,
25 H), 0.91 (d, J = 6.5 Hz, 3 H), 0.87 (d, J = 6.6 Hz, 3 H), 0.86 (d, J = 6.5 Hz, 3 H), 0.68 (s, 3
H); 13C NMR (125 MHz, CDCl3) δ 159.1, 141.1, 131.3, 129.1, 121.5, 113.8, 78.3, 69.6, 56.8,
56.2, 55.3, 50.2, 42.4, 39.8, 39.5, 39.2, 37.3, 36.9, 36.2, 35.8, 32.0, 31.9, 28.5, 28.2, 28.0,
24.3, 23.8, 22.8, 22.6, 21.1, 19.4, 18.7, 11.9.
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1-(4-Methoxybenzyloxy)-3-phenylprop-2-ene (1e)20: According to general procedure 1,
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cinnamyl alcohol 2e (537 mg, 4 mmol) gave 1e (865 mg, 85 %) as a colorless oil. H NMR
(300 MHz, CDCl3) δ 7.44ꢀ7.20 (m, 7 H), 6.90 (d, J = 8.7 Hz, 2 H), 6.62 (td, J = 1.5, 15.8 Hz,
1 H), 6.33 (td, J = 6.0, 15.8 Hz, 1 H), 4.51 (s, 2 H), 4.18 (dd, J = 1.5, 6.0 Hz, 2 H), 3.61 (s, 3
H); 13C NMR (75 MHz, CDCl3) δ 159.2, 136.8, 132.5, 130.4, 129.5, 128.6, 127.7, 126.5,
126.2, 113.9, 71.9, 70.5, 55.3.
1-(4-Methoxybenzyloxy)-cyclohex-2-ene (1f)21: According to general procedure 1,
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cyclohexꢀ2ꢀenꢀ1ꢀol 2f (300 mg, 3.05 mmol) gave 1f (426 mg, 65%) as a colorless oil. H
NMR (300 MHz, CDCl3) δ 7.29 (d, J = 8.6 Hz, 2 H), 6.88 (d, J = 8.6 Hz, 2 H), 5.94ꢀ5.70 (m,
2 H), 4.53 (d, J = 11.6 Hz, 1 H), 4.47 (d, J = 11.6 Hz, 1 H), 4.00ꢀ3.87 (m, 1 H), 3.79 (s, 3 H),
2.16ꢀ1.44 (m, 6 H); 13C NMR (75 MHz, CDCl3) δ 159.0, 131.1, 130.7, 129.1, 127.9, 113.7,
71.8, 69.6, 55.2, 28.4, 25.2, 19.3.
1-(4-Methoxybenzyloxy)-undec-10-ene (1g)22: According to general procedure 1, undecꢀ10ꢀ
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enꢀ1ꢀol 2g (1 g, 5.87 mmol) gave 1g as a yellow oil (1.05 g, 62%). H NMR (300 MHz,
CDCl3) δ 7.26 (d, J = 8.6 Hz, 2 H), 6.88 (d, J = 8.6 Hz, 2 H), 5.88ꢀ5.75 (m, 1 H), 4.99 (dq, J =
17.1, 1.7 Hz, 1 H), 4.93 (dquint, J = 10.3, 1.1 Hz, 1 H), 4.48 (s, 2H), 3.80 (s, 3 H), 3.43 (t, J =
6.8 Hz, 2 H), 2.04 (dt, J = 7.8, 6.8 Hz, 2 H), 1.64ꢀ1.51 (m, 2 H), 1.44ꢀ1.31 (m, 4 H), 1.31ꢀ1.23
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(m, 8 H); C NMR (75 MHz, CDCl3) δ 159.1, 139.3, 130.1, 129.2, 114.1, 113.8, 72.5, 70.3,
55.3, 33.8, 29.8, 29.6, 29.5, 29.2, 29.0, 26.2.
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