3054 (aromatic CH), 2957 (aliphatic CH), 2870 (aldehyde CH),
2732 (aldehyde CH), 1658 (CO), 1476; δH (300 MHz; CDCl3)
1.36 (9H, s, But), 1.45 (9H, s, But), 6.83 (1H, s, aromatic), 10.28
(1H, s, aldehyde); δC (75 MHz; CDCl3) 182.97, 166.50, 160.21,
135.47, 124.24, 35.28, 35.14, 33.06, 31.89; m/z 224.1234
(C13H20OS requires Mr, 224.1235).
1678 (CO), 1630, 1596, 1470, 1287, 791, 704; δH (300 MHz;
CDCl3) 1.36 (9H, s, But), 6.97 (2H, t, J 7.7 Hz, aromatic), 7.39–
7.49 (2H, m, aromatic), 8.11 (1H, dd, J 2.2, 8.3 Hz, aromatic),
8.88 (1H, br s, aromatic); δC (75 MHz; CDCl3) 187.48, 174.99,
161.45, 161.34, 158.11, 158.01, 150.51, 136.69, 132.47, 132.36,
132.20, 129.50, 119.26, 112.14, 111.81, 38.15, 29.86; m/z
275.1128 (C16H15F2NO requires Mr, 275.1122).
1-[5-(1,1-Dimethylethyl)-2-thienyl]ethanone. Colorless liquid;
TLC (30% ethyl acetate–hexane) Rf 0.60; νmax/cmϪ1 3049
(aromatic CH), 2934 (aliphatic CH), 1670 (CO), 1599, 1445;
δH (300 MHz; CDCl3) 1.35 (9H, s, But), 2.47 (3H, s, acetyl), 6.83
(1H, d, J 3.8 Hz, aromatic), 7.49 (1H, d, J 3.8 Hz, aromatic);
δC (75 MHz; CDCl3) 190.74, 167.35, 141.23, 132.63, 122.86,
35.16, 32.13, 26.45; m/z 182.0767 (C10H14OS requires Mr,
182.0765).
[5-(1,1-Dimethylethyl)-2-thienyl]phenylmethanone. Colorless
liquid; TLC (30% ethyl acetate–hexane) Rf 0.61; νmax/cmϪ1 3056
(aromatic CH), 2954 (aliphatic CH), 1635 (CO), 1532, 1453;
δH (300 MHz; CDCl3) 1.40 (9H, s, But), 6.88 (1H, d, J 4.0 Hz,
aromatic), 7.42–7.47 (3H, m, aromatic), 7.51–7.56 (1H, m,
aromatic), 7.81 (2H, d, J 7.0 Hz, aromatic); δC (75 MHz;
CDCl3) 188.07, 167.70, 140.20, 138.16, 135.15, 131.82, 128.90,
128.20, 122.81, 35.12, 32.05; m/z 244.0922 (C15H16OS requires
Mr, 244.0922).
2-(1,1-Dimethylethyl)-5-phenylpyridine. Colorless liquid;
TLC (30% ethyl acetate–hexane) Rf 0.75; νmax/cmϪ1 3034
(aromatic CH), 2964 (aliphatic CH), 1599, 1486, 760, 703;
δH (300 MHz; CDCl3) 1.40 (9H, s, But), 7.34–7.47 (4H, m,
aromatic), 7.54–7.58 (2H, m, aromatic), 7.79 (1H, dd, J 2.0, 8.3
Hz, aromatic), 8.79 (1H, d, J 2.0 Hz, aromatic); δC (75 MHz;
CDCl3) 168.17, 146.97, 138.02, 134.56, 133.45, 128.96, 127.66,
126.95, 118.94, 37.19, 30.19; m/z 211.1362 (C15H17N1 requires
Mr, 211.1361).
Acknowledgements
The financial support for this project was provided from Korea
Science and Engineering Foundation (2000-1-12400-001-5).
B. H. K. acknowledges Kwangwoon University and the
University of Oregon (Prof. Kenneth M. Doxsee) for his
sabbatical.
[6-(1,1-Dimethylethyl)pyridin-3-yl]phenylmethanone. Color-
less liquid; TLC (30% ethyl acetate–hexane) Rf 0.62; νmax/cmϪ1
3053 (aromatic CH), 2957 (aliphatic CH), 1666 (CO), 1595,
1484, 1306; δH (300 MHz; CDCl3) 1.40 (9H, s, But), 7.46–7.60
(4H, m, aromatic), 7.81 (2H, d, J 8.3 Hz, aromatic), 8.06 (1H,
dd, J 2.2, 8.3 Hz, aromatic), 8.94 (1H, d, J 2.2 Hz, aromatic);
δC (75 MHz; CDCl3) 194.77, 173.26, 150.02, 137.63, 136.94,
132.80, 130.20, 129.87, 128.42, 118.84, 37.89, 29.93; m/z
239.1316 (C16H17NO requires Mr, 239.1310).
References
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[6-(1,1-Dimethylethyl)pyridin-3-yl](3-fluorophenyl)methanone.
Colorless liquid; TLC (30% ethyl acetate–hexane) Rf 0.68;
νmax/cmϪ1 3051 (aromatic CH), 2967 (aliphatic CH), 1674 (CO),
1590, 1451, 1300, 860, 792, 704; δH (300 MHz; CDCl3) 1.38
(9H, s, But), 7.25–7.32 (1H, m, aromatic), 7.42–7.57 (4H, m,
aromatic), 8.04 (1H, dd, J 2.2, 8.3 Hz, aromatic), 8.91 (1H, d,
J 2.2 Hz, aromatic); δC (75 MHz; CDCl3) 193.52, 173.83,
164.21, 160.92, 150.09, 139.13, 139.04, 137.51, 130.21, 130.11,
129.73, 125.73, 125.69, 119.99, 119.71, 118.95, 116.72, 116.42,
38.01, 29.95; m/z 257.1207 (C16H16FNO requires Mr, 257.1216).
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(2,6-Difluorophenyl)[6-(1,1-dimethylethyl)pyridin-3-yl]-
methanone. Colorless liquid; TLC (30% ethyl acetate–hexane)
Rf 0.63; νmax/cmϪ1 3070 (aromatic CH), 2965 (aliphatic CH),
15 M. Tiecco, Acc. Chem. Res., 1980, 13, 51.
J. Chem. Soc., Perkin Trans. 1, 2001, 2035–2039
2039