314
J.-L. Yu et al. / Tetrahedron 69 (2013) 310e315
127.2, 113.8, 77.5, 68.7, 55.3, 32.0, 30.1, 29.3, 26.3, 24.3, 22.7, 14.2;
HR-MS (ESI) m/z¼273.1815, calcd for C16H26O2Na [MþNa]þ:
273.1830.
62.0, 55.3, 23.9; HR-MS (ESI) m/z¼219.0999, calcd for C11H16O3Na
[MþNa]þ: 219.0997.
4.3.12. 1-(1-Butoxyethyl)-3-methoxybenzene (4m). Colorless oil,
4.3.3. 1-(1-Dodecyloxyethyl)-4-methoxybenzene (4c). Colorless oil,
78% yield. 1H NMR (400 MHz, CDCl3)
d 7.23 (s, 1H), 6.88e6.79 (m,
77% yield. 1H NMR (400 MHz, CDCl3)
d
7.23 (d, J¼7.6 Hz, 2H), 6.87 (d,
3H), 4.36 (q, J¼6.1 Hz, 1H), 3.82 (s, 3H), 3.30 (t, J¼6.8 Hz, 2H), 1.56
J¼7.6 Hz, 2H), 4.33 (q, J¼6.4 Hz, 1H), 3.80 (s, 3H), 3.25 (t, J¼6.4 Hz,
2H), 1.54e1.52 (m, 2H), 1.41 (d, J¼6.0 Hz, 3H), 1.29e1.24 (m, 18H),
(br s, 2H), 1.42 (d, J¼6.0 Hz, 3H), 1.37e1.34 (m, 2H), 0.89 (t, J¼6.9 Hz,
3H); 13C NMR (100 MHz, CDCl3)
d 159.9, 146.3, 129.4, 118.6, 112.8,
0.88 (t, J¼6.7 Hz, 3H); 13C NMR (100 MHz, CDCl3)
d
159.0, 136.5,
111.5, 77.9, 68.6, 55.2, 32.3, 24.3, 19.5, 14.0; HR-MS (ESI) m/
127.4, 113.8, 77.5, 68.7, 55.4, 32.1, 30.1, 29.7, 29.6, 29.5, 26.3, 24.3,
22.8, 14.3; HR-MS (ESI) m/z¼343.2608, calcd for C21H36O2Na
[MþNa]þ: 343.2613.
z¼231.1335, calcd for C13H20O2Na [MþNa]þ: 231.1361.
4.3.13. 1-(1-Heptyloxyethyl)-4-methylbenzene (4n). Colorless oil,
71% yield. 1H NMR (400 MHz, CDCl3)
d 7.25e7.14 (m, 4H), 4.34 (q,
4.3.4. 1-Methoxy-4-(1-(octadecyloxy)ethyl)benzene (4d). Colorless
J¼6.2 Hz, 1H), 3.26 (t, J¼6.4 Hz, 2H), 2.34 (s, 3H), 1.55e1.53 (m, 2H),
oil, 85% yield. 1H NMR (400 MHz, CDCl3)
d
7.23 (d, J¼8.3 Hz, 2H),
1.41 (d, J¼6.3 Hz, 3H), 1.30e1.24 (m, 8H), 0.87 (t, J¼5.5 Hz, 3H); 13C
6.88 (d, J¼8.4 Hz, 2H), 4.33 (q, J¼6.3 Hz, 1H), 3.80 (s, 3H), 3.25 (t,
NMR (100 MHz, CDCl3) d 141.4, 136.9, 129.1, 126.2, 77.8, 68.8, 32.0,
J¼6.6 Hz, 2H), 1.54e1.50 (m, 2H), 1.41 (d, J¼6.3 Hz, 3H), 1.30e1.25
30.1, 29.3, 26.3, 24.4, 22.7, 21.2, 14.2; HR-MS (ESI) m/z¼257.1873,
(m, 30H), 0.88 (t, J¼7.0 Hz, 3H); 13C NMR (100 MHz, CDCl3)
d 159.0,
calcd for C16H26ONa [MþNa]þ: 257.1881.
136.5, 127.4, 113.8, 77.5, 68.7, 55.4, 32.1, 30.1, 29.9, 29.8, 29.6, 29.5,
26.4, 24.3, 22.8, 14.3; HR-MS (ESI) m/z¼427.3553, calcd for
C27H48O2Na [MþNa]þ: 427.3552.
4.3.14. 1-(1-sec-Butoxyethyl)-4-methylbenzene (4o). Colorless oil,
75% yield. 1H NMR (400 MHz, CDCl3)
d 7.24e7.12 (m, 4H), 4.51 (q,
J¼6.5 Hz, 0.5ꢁ 1H), 4.48 (d, J¼6.5 Hz, 0.5ꢁ 1H), 3.35e3.29 (m, 0.5ꢁ
1H), 3.23e3.16 (m, 0.5ꢁ 1H), 2.34 (s, 3H), 1.55e1.38 (m, 2H), 1.40 (d,
J¼6.5 Hz, 0.5ꢁ 3H), 1.39 (d, J¼6.5 Hz, 0.5ꢁ 3H), 1.11 (d, J¼6.0 Hz,
0.5ꢁ 3H), 1.03 (d, J¼6.3 Hz, 0.5ꢁ 3H), 0.89 (t, J¼7.4 Hz, 0.5ꢁ 3H),
4.3.5. 1-(1-Isopentyloxyethyl)-4-methoxybenzene (4e).5a Colorless
oil, 83% yield. 1H NMR (400 MHz, CDCl3)
d
7.23 (d, J¼7.7 Hz, 2H),
6.87 (d, J¼7.6 Hz, 2H), 4.33 (q, J¼6.6 Hz, 1H), 3.81 (s, 3H), 3.27 (t,
J¼6.6 Hz, 2H), 1.69e1.62 (m, 1H), 1.45 (d, J¼7.2 Hz, 3H), 1.46e1.25
(m, 2H), 0.86 (d, J¼6.5 Hz, 3H), 0.83 (d, J¼6.5 Hz, 3H).
0.80 (t, J¼7.4 Hz, 0.5ꢁ 3H); 13C NMR (100 MHz, CDCl3)
d 142.1, 141.7,
136.9, 136.8, 129.0, 126.4, 126.2, 75.2, 74.3, 74.0, 73.3, 30.4, 28.5,
24.9, 24.8, 24.6, 21.2, 20.4, 18.9, 10.3, 9.5; HR-MS (ESI) m/
z¼215.1405, calcd for C13H20ONa [MþNa]þ: 215.1412.
4.3.6. 1-(1-Allyloxyethyl)-4-methoxybenzene (4f).13 Colorless oil,
81% yield. 1H NMR (400 MHz, CDCl3)
d
7.24 (d, J¼8.0 Hz, 2H), 6.88
(d, J¼7.5 Hz, 2H), 5.93e5.86 (m, 1H), 5.23 (d, J¼17.2 Hz, 1H), 5.14 (d,
J¼10.2 Hz, 1H), 4.42 (q, J¼6.3 Hz, 1H), 3.86 (d, J¼8.2 Hz, 2H), 3.80 (s,
3H), 1.44 (d, J¼6.2 Hz, 3H).
4.3.15. 1-(2-Butoxypropan-2-yl)benzene (4p).2b Colorless oil, 48%
yield. 1H NMR (400 MHz, CDCl3)
d 7.42e7.21 (m, 5H), 3.14 (t,
J¼6.7 Hz, 2H), 1.53 (s, 6H), 1.50e1.48 (m, 2H), 1.35e1.28 (m, 2H),
0.87 (t, J¼7.3 Hz, 3H).
4.3.7. 1-(1-sec-Butoxyethyl)-4-methoxybenzene (4g).7n Colorless oil,
75% yield. 1H NMR (400 MHz, CDCl3)
d
7.24 (d, J¼7.6 Hz, 2H), 6.87 (d,
4.4. Characterization for 6a and 6b
J¼7.9 Hz, 2H), 4.51e4.44 (m, 1H), 3.80 (s, 3H), 3.33e3.29 (m, 0.5ꢁ
1H), 3.22e3.17 (m, 0.5ꢁ 1H), 1.55e1.33 (m, 2H), 1.39 (d, J¼6.3 Hz,
3H), 1.11 (d, J¼5.4 Hz, 0.5ꢁ 3H), 1.02 (d, J¼5.4 Hz, 0.5ꢁ 3H), 0.89 (t,
J¼7.2 Hz, 0.5ꢁ 3H), 0.80 (t, J¼7.2 Hz, 0.5ꢁ 3H).
4.4.1. 2-Phenyl-tetrahydrofuran (6a).12 Colorless oil, 72% yield. 1H
NMR (400 MHz, CDCl3)
4.13e4.08 (m, 1H), 3.91e3.97 (m, 1H), 2.35e2.29 (m, 1H), 2.05e1.96
(m, 2H), 1.85e1.76 (m, 1H).
d
7.34e7.21 (m, 5H), 4.89 (t, J¼7.2 Hz, 1H),
4.3.8. 1-(1-Isopropoxyethyl)-4-methoxybenzene (4h).14 Colorless oil,
53% yield. 1H NMR (400 MHz, CDCl3)
d
7.28 (d, J¼8.4 Hz, 2H), 6.91
4.4.2. 2-Phenyl-tetrahydro-2H-pyran (6b).12 Colorless oil, 18% yield.
1H NMR (400 MHz, CDCl3)
1H), 4.14 (d, J¼9.7 Hz, 1H), 3.60 (t, J¼11.2 Hz, 1H), 1.93e1.82 (m, 1H),
1.69e1.65 (m, 1H), 1.62e1.58 (m, 4H).
d
7.35e7.32 (m, 5H), 4.32 (d, J¼8.9 Hz,
(d, J¼8.0 Hz, 2H), 4.52 (q, J¼6.3 Hz, 1H), 3.84 (s, 3H), 3.53e3.47
(m, 1H), 1.42 (d, J¼6.3 Hz, 3H), 1.17 (d, J¼5.8 Hz, 3H), 1.11 (d,
J¼6.0 Hz, 3H).
4.3.9. 1-Methoxy-4-(1-methoxyethyl)benzene (4j).13 Colorless oil,
Acknowledgements
87% yield. 1H NMR (400 MHz, CDCl3)
d
7.23 (d, J¼7.6 Hz, 2H), 6.88 (d,
J¼7.5 Hz, 2H), 4.25 (q, J¼5.9 Hz, 1H), 3.81 (s, 3H), 3.19 (s, 3H), 1.42
(d, J¼5.8 Hz, 3H).
This work was supported by the National Natural Science
Foundation of China (Project No. 21102017), and Fudan University
Youth Scientific Foundation. D.-W.Z. thanks Fudan University for
the conferment of the Century Star Award.
4.3.10. 5-((1-(4-Methoxyphenyl)ethoxy)methyl)benzo[d][1,3]dioxole
(4k). Colorless oil, 87% yield. 1H NMR (400 MHz, CDCl3)
d 7.26 (d,
J¼8.6 Hz, 2H), 6.90 (d, J¼8.1 Hz, 2H), 6.82 (s, 1H), 6.75 (d, J¼7.8 Hz,
1H), 6.72 (d, J¼7.8 Hz, 1H), 5.93 (s, 2H), 4.42 (q, J¼6.4 Hz, 1H), 4.23
(AB, JAB¼11.4 Hz, 2H), 3.82 (s, 3H), 1.44 (d, J¼6.7 Hz, 3H); 13C NMR
Supplementary data
Supplementary data related to this article can be found at http://
(100 MHz, CDCl3) d 159.1, 147.7,147.0, 135.7, 132.6, 127.6, 121.3, 113.9,
108.6, 108.1, 100.9, 76.5, 69.9, 55.3, 24.2; HR-MS (ESI) m/z¼309.1110,
calcd for C17H18O4Na [MþNa]þ: 309.1103.
References and notes
4.3.11. 2-(1-(4-Methoxyphenyl)ethoxy)ethanol (4l). Colorless oil,
€
1. (a) Williamson, A. W. J. Chem. Soc. 1852, 229e239; (b) Edgar, F.; Jorg, T. Org.
Process Res. Dev. 2005, 9, 206e211.
72% yield. 1H NMR (400 MHz, CDCl3)
d
7.23 (d, J¼7.6 Hz, 2H), 6.88 (d,
2. (a) Feuer, H.; Hooz, J. In The Chemistry of the Ether Linkage; Wiley: New York, NY,
1967; pp 457e460; 468e470; (b) Boyer, B.; Keramane, E.-M.; Roque, J.-P.; Pavia,
A. A. Tetrahedron Lett. 2000, 41, 2891e2894; (c) Olah, G. A.; Fung, A. P.; Mal-
hotra, R. Synthesis 1981, 474e476.
J¼7.4 Hz, 2H), 4.40 (q, J¼6.2 Hz, 1H), 3.81 (s, 3H), 3.68 (d, J¼1.8 Hz,
2H), 3.40 (d, J¼1.8 Hz, 2H), 2.04e1.99 (m, 1H), 1.45 (d, J¼6.1 Hz, 3H);
13C NMR (100 MHz, CDCl3)
d 159.1, 135.4, 127.5, 113.9, 78.0, 69.6,