Page 15 of 21
The Journal of Organic Chemistry
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eluant, 1e was obtained as a colorless liquid; 1H NMR (300 MHz, CDCl3) δ 7.27 (d, 2H), 6.87 (d, 2H), 4.44 (s, 2H),
3.80 (s, 3H), 3.58 – 3.43 (m, 1H), 1.74 – 1.46 (m, 4H), 1.43 – 1.21 (m, 18H); 13C NMR (75 MHz, CDCl3) δ 159.1,
131.5, 129.4, 113.8, 76.0, 70.0, 55.4, 29.0, 24.7, 24.3, 23.4, 23.2, 20.9.
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(3s,5s,7s)-1-((4-Methoxybenzyl)oxy)adamantane (1f).6b Following the general procedure using 5% ethyl acetate in
hexanes as eluant, 1f was obtained as a white solid; 1H NMR (300 MHz, CDCl3) δ 7.28 (d, 2H), 6.87 (d, 2H), 4.44 (s,
2H), 3.79 (s, 3H), 2.24 – 2.07 (m, 2H), 1.85 (d, 6H), 1.69 – 1.50 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 158.9, 132.3,
129.1, 113.8, 72.7, 62.1, 55.4, 41.9, 36.6, 30.7.
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(3S,5S,8R,9S,10S,13R,14S,17R)-3-((4-Methoxybenzyl)oxy)-10,13-dimethyl-17-((R)-6-methylheptan-2-
yl)hexadecahydro-1H-cyclopenta[a]phenanthrene (1g).36 Following the general procedure using 5% ethyl acetate in
hexanes as eluant, 1g was obtained as a white solid; 1H NMR (300 MHz, CDCl3) δ 7.34 – 7.23 (m, 2H), 6.94 – 6.83
(m, 2H), 4.50 (s, 2H), 3.82 (s, 3H), 3.42 – 3.23 (m, 1H), 2.08 – 0.96 (m, 30H), 0.92 (d, J = 6.5 Hz, 3H), 0.90 (d, J =
1.4 Hz, 3H), 0.88 (d, J = 1.4 Hz, 3H), 0.82 (s, 4H), 0.67 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 159.1, 131.4, 129.3,
113.9, 77.9, 69.5, 56.6, 56.4, 55.4, 54.6, 45.0, 42.7, 40.2, 39.7, 37.2, 36.3, 35.9, 35.6, 35.0, 32.3, 29.0, 28.4, 28.4, 28.2,
24.4, 24.0, 23.0, 22.7, 21.4, 18.8, 12.4, 12.2.
1-(((5-(Benzyloxy)pentyl)oxy)methyl)-4-methoxybenzene (1h).20 Following the general procedure using 8% ethyl
acetate in hexanes as eluant, 1h was obtained as a colorless liquid; 1H NMR (300 MHz, CDCl3) δ 7.38 – 7.28 (m,
5H), 7.25 (d, J = 8.6 Hz, 2H), 6.87 (d, 2H), 4.49 (s, 2H), 4.42 (s, 2H), 3.80 (s, 3H), 3.45 (dt, J = 8.3, 6.6 Hz, 4H), 1.62
(tt, J = 6.6, 3.3 Hz, 4H), 1.51 – 1.37 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 159.2, 138.8, 130.9, 129.4, 128.5, 127.8,
127.6, 113.9, 73.0, 72.7, 70.5, 70.1, 55.4, 29.7, 23.0.
5-((4-Methoxybenzyl)oxy)pentyl acetate (1i).20 Following the general procedure using 7% ethyl acetate in hexanes as
eluant, 1i was obtained as a colorless liquid; 1H NMR (300 MHz, CDCl3) δ 7.26 (d, 2H), 6.87 (d, 2H), 4.43 (s, 2H),
4.05 (t, J = 6.6 Hz, 2H), 3.80 (s, 3H), 3.44 (t, J = 6.4 Hz, 2H), 2.04 (s, 3H), 1.70 – 1.60 (m, 4H), 1.51 – 1.37 (m, 2H);
13C NMR (75 MHz, CDCl3) δ 171.4, 159.2, 130.7, 129.4, 113.9, 72.7, 69.9, 64.6, 55.4, 29.5, 28.5, 22.8, 21.1.
6-((4-Methoxybenzyl)oxy)hexyl benzoate (1j).20 Following the general procedure using 5% ethyl acetate in hexanes
as eluant, 1j was obtained as a slightly yellow liquid; 1H NMR (300 MHz, CDCl3) δ 8.22 – 8.13 (m, 1H), 8.08 – 8.01
(m, 2H), 7.48 – 7.39 (m, 2H), 7.31 – 7.22 (m, 2H), 6.94 – 6.81 (m, 2H), 4.43 (s, 2H), 4.31 (t, J = 6.6 Hz, 2H), 3.80 (s,
3H), 3.45 (t, J = 6.5 Hz, 2H), 1.76 (d, J = 7.0 Hz, 2H), 1.63 (t, J = 6.7 Hz, 2H), 1.51 – 1.38 (m, 4H); 13C NMR (75
MHz, CDCl3) δ 159.2, 132.9, 130.7, 130.6, 129.7, 129.4, 129.0, 128.5, 113.9, 72.7, 70.1, 65.2, 55.4, 29.8, 28.8, 26.1.
6-((4-Methoxybenzyl)oxy)hexyl pivalate (1k).6a Following the general procedure using 5% ethyl acetate in hexanes
as eluant, 1k was obtained as a slightly yellow liquid; 1H NMR (300 MHz, CDCl3) δ 7.31 – 7.20 (dd, 2H), 6.93 – 6.82
(dd, 2H), 4.43 (s, 2H), 4.04 (t, J = 6.6 Hz, 2H), 3.80 (s, 3H), 3.43 (t, J = 6.5 Hz, 2H), 1.62 (m, J = 4.5 Hz, 4H), 1.41 –
1.32 (m, 4H), 1.19 (s, 9H); 13C NMR (75 MHz, CDCl3) δ 178.8, 159.2, 130.8, 129.4, 113.9, 72.7, 70.1, 64.5, 55.4,
38.8, 29.8, 28.7, 27.3, 26.0, 25.9.
2-((6-((4-Methoxybenzyl)oxy)hexyl)oxy)tetrahydro-2H-pyran (1l).6a Following the general procedure using 10%
ethyl acetate in hexanes as eluant, 1l was obtained as a colorless liquid; 1H NMR (300 MHz, CDCl3) δ 7.30 – 7.22 (m,
2H), 6.91 – 6.84 (m, 2H), 4.56 (t, J = 4.6, 2.7 Hz, 1H), 4.43 (s, 2H), 3.91 – 3.82 (m, 1H), 3.80 (s, 3H), 3.78 – 3.67 (m,
1H), 3.55 – 3.46 (m, 1H), 3.43 (t, J = 6.6 Hz, 2H), 3.40 – 3.32 (m, 1H), 1.88 – 1.64 (m, 3H), 1.64 – 1.45 (m, 7H), 1.43
– 1.32 (m, 4H);13C NMR (75 MHz, CDCl3) δ 159.2, 130.9, 129.3, 113.8, 99.0, 72.6, 70.2, 67.7, 62.5, 55.4, 30.9, 29.8,
26.2, 26.2, 25.6, 19.8.
Tert-butyl((5-((4-methoxybenzyl)oxy)pentyl)oxy)dimethylsilane (1m).6a Following the general procedure using 6%
ethyl acetate in hexanes as eluant, 1m was obtained as a colorless liquid; 1H NMR (300 MHz, CDCl3) δ 7.30 – 7.22
(m, 2H), 6.91 – 6.84 (m, 2H), 4.43 (s, 2H), 3.80 (s, 3H), 3.60 (t, J = 6.5 Hz, 2H), 3.44 (t, J = 6.6 Hz, 2H), 1.68 – 1.49
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