The Journal of Organic Chemistry
Note
1-(Benzo[d][1,3]dioxol-5-yl)pentan-3-one (3ja, 194 mg,
REFERENCES
1
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94%). Colorless liquid. H NMR (400 MHz, CDCl3) δ 6.71 (d, J =
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7.6 Hz, 1H), 6.67−6.66 (m, 1H), 6.63−6.61 (m, 1H), 5.91 (s, 2H),
2.81 (t, J = 7.4 Hz, 2H), 2.68 (t, J = 7.4 Hz, 2H), 2.39 (q, J = 7.2 Hz,
2H), 1.04 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 210.8,
147.8, 146.0, 135.2, 121.2, 109.0, 108.4, 101.0, 44.3, 36.3, 29.8, 8.0.
HRMS (QTOF-ESI) calcd for C12H14O3Na (M + Na) 229.0841,
found 229.0801.
1-Phenylpentan-3-one (3ka, 143 mg, 89%).22 Colorless liquid.
1H NMR (400 MHz, CDCl3) δ 7.30−7.26 (m, 2H), 7.22−7.14 (m,
3H), 2.91 (t, J = 7.6 Hz, 2H), 2.73 (t, J = 7.6 Hz, 2H), 2.41 (q, J = 7.2
Hz, 2H), 1.05 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ
210.8, 141.4, 128.7, 128.6, 126.3, 44.1, 36.3, 30.1, 8.0.
(E)-7-Phenylhept-6-en-3-one (3la, 108 mg, 57%).23 Colorless
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4229.
1
liquid. H NMR (400 MHz, CDCl3) δ 7.35−7.27(m, 4H), 7.22−7.18
(m, 1H), 6.41 (d, J = 15.6 Hz, 1H), 6.24−6.18 (m, 1H), 2.64−2.57
(m, 2H), 2.51−2.42 (m, 4H), 1.07 (t, J = 7.4 Hz, 3H). 13C NMR (100
MHz, CDCl3) δ 211.0, 137.7, 130.9, 129.3, 128.8, 127.3, 126.2, 42.0,
36.3, 27.4, 8.1.
(5) (a) Tian, P.; Dong, H.-Q.; Lin, G.-Q. ACS Catal. 2012, 2, 95.
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Karaghiosoff, K.; Mayer, P.; Knochel, P. Org. Lett. 2011, 13, 3182.
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Xu, M.-H. Org. Biomol. Chem. 2012, 10, 1764. (f) Sasaki, K.;
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3-(4-(tert-Butyl)phenyl)-1-(p-tolyl)propan-1-one (3ab, 190
mg, 68%; 258 mg, 92%). White solid (mp 63.6−64.0 °C). 1H
NMR (400 MHz, CDCl3) δ 7.87 (d, J = 8.0 Hz, 2H), 7.35−7.32 (m,
2H), 7.27−7.19 (m, 4H), 3.28 (t, J = 7.6 Hz, 2H), 3.04 (t, J = 7.6 Hz,
2H), 2.41 (s, 3H), 1.32 (s, 9H). 13C NMR (100 MHz, CDCl3) δ
199.3, 149.1, 144.0, 138.6, 134.7, 129.5, 128.4, 128.4, 125.7, 40.6, 34.6,
31.7, 29.9, 21.9. HRMS (QTOF-ESI) calcd for C20H25O (M + H)
281.1905, found 281.1869.
(6) (a) Gutnov, A. Eur. J. Org. Chem. 2008, 4547. (b) Miyaura, N.
Synlett 2009, 2039.
1-(4-(tert-Butyl)phenyl)-5-phenylpentan-3-one (3ac, 270
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768−769. (b) Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9,
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1
mg, 92%). Colorless viscous oil. H NMR (400 MHz, CDCl3) δ
7.32−7.26 (m, 4H), 7.22−7.15 (m, 3H), 7.13−7.08 (m, 2H), 2.91−
2.84 (m, 4H), 2.73−2.69 (m, 4H), 1.31 (s, 9H). 13C NMR (100 MHz,
CDCl3) δ 209.6, 149.2, 141.3, 138.2, 128.8, 128.6, 128.2, 126.4, 125.6,
44.8, 34.6, 31.7, 30.0, 29.5. HRMS (QTOF-ESI) calcd for C21H26ONa
(M + Na) 317.1881, found 317.1868.
n-Butyl 3-(4-(tert-Butyl)phenyl)propanoate (3ad, 196 mg,
1
75%). Colorless oil. H NMR (400 MHz, CDCl3) δ 7.33−7.29 (m,
2H), 7.24−7.20 (m, 3H), 4.09 (t, J = 8.0 Hz, 2H), 2.98 (t, J = 8.0 Hz,
2H), 2.65 (t, J = 8.0 Hz, 2H), 1.57−1.62 (m, 2H), 1.33−1.39 (m, 2H),
0.92 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 173.4, 149.2,
128.2, 126.1, 125.6, 64.5, 36.2, 31.6, 31.4, 30.9, 30.7, 19.4, 14.0. HRMS
(QTOF-ESI) calcd for C17H26O2Na (M + Na) 285.1831, found
285.1837.
3-(4-(tert-Butyl)phenyl)cyclopentanone (3ae, 89 mg, 41%;
166 mg, 77%). Beige solid (mp 79.9−80.3 °C). 1H NMR (400 MHz,
CDCl3) δ 7.40−7.34 (m, 2H), 7.23−7.15 (m, 2H), 3.44−3.35 (m,
1H), 2.69−2.63 (m, 1H), 2.50−2.43 (m, 2H), 2.38−2.45 (m, 2H),
2.04−1.93 (m, 1H), 1.32 (s, 9H). 13C NMR (100 MHz, CDCl3) δ
218.7, 149.8, 140.3, 126.7, 125.8, 46.1, 42.0, 39.2, 34.7, 31.7, 31.5.
HRMS (QTOF-ESI) calcd for C15H21O (M + H) 217.1592, found
217.1573.
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ASSOCIATED CONTENT
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S
* Supporting Information
NMR and/or HPLC spectra of compounds 1−3. This material
(16) Bodwell, G. J.; Li, J.; Miller, D. O. Tetrahedron 1999, 55, 12939.
(17) Molander, G. A.; Jean-Gerard, L. J. Org. Chem. 2009, 74, 1297.
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AUTHOR INFORMATION
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Corresponding Author
(18) Jana, R.; Tunge, J. A. Org. Lett. 2009, 11, 971.
(19) Molander, G. A.; Petrillo, D. E. Org. Lett. 2008, 10, 1795.
(20) Shen, Z.-L.; Lai, Y.-C.; Wong, C. H. A.; Goh, K. K. K.; Yang, Y.-
S.; Cheong, H.-L.; Loh, T.-P. Org. Lett. 2010, 13, 422.
(21) Chen, M.; Wang, J.; Chai, Z.; You, C.; Lei, A. Adv. Synth. Catal.
2012, 354, 341.
Notes
The authors declare no competing financial interest.
(22) Lee, D.-Y.; Hong, B.-S.; Cho, E.-G.; Lee, H.; Jun, C.-H. J. Am.
Chem. Soc. 2003, 125, 6372.
(23) Jana, R.; Tunge, J. A. Org. Lett. 2009, 11, 971.
ACKNOWLEDGMENTS
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We thank the National Natural Science Foundation of China
for financial support.
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dx.doi.org/10.1021/jo4001367 | J. Org. Chem. XXXX, XXX, XXX−XXX