A. Sharma et al. / Tetrahedron 62 (2006) 847–851
851
6.83 (1H, s, H-6), 6.76 (2H, m, H-2 and H-50), 5.91 (2H, s,
Supplementary data
–OCH2O–), 1.79–1.73 (4H, m, H-20 and H-2 ), 0.89 (6H, t,
JZ6.9 Hz, H-30 and H-30); 13C NMR (CDCl3, 75.4 MHz): d
149.0 (C-3), 148.2 (C-4), 134.5 (C-1), 121.6 (C-6), 112.3
(C-5), 105.1 (C-2), 98.5 (–OCH2O–), 77.1 (C-10), 30.7 (C-20
and C-20), 11.4 (C-30 and C-30); HRMS (negative) m/z:
207.2419 (Calcd for C12H16O3: 207.2493).
Supplementary data associated with this article can be
4.2.6. Compound 1f. Colourless liquid, 1.8 g (8%); nmax
References and notes
1
(CHCl3) 3571 cmK1; H NMR (CDCl3, 300 MHz): d 7.20
(1H, d, JZ8.5 Hz, H-6), 6.5 (1H, d, JZ8.5 Hz, H-5), 6.39
(1H, s, H-3), 3.69 (6H, s, 2 and 4 –OCH3), 1.71–1.69 (4H,
m, H-20 and H-20), 0.92 (6H, t, JZ7.3 Hz, H-30 and H-30);
13C NMR (CDCl3, 75.4 MHz): d 159.7 (C-2), 158.8 (C-4),
129.4 (C-6), 117.2 (C-1), 102.2 (C-5), 99.1 (C-3), 72.6
(C-10), 55.8 (2-OCH3), 55.2 (4-OCH3), 33.1 (C-20 and C-20),
8.1 (C-30 and C-30); HRMS (positive) m/z: 225.3012 (Calcd
for C13H20O3: 225.3079).
1. (a) Neil, H. A.; Mant, D.; Jones, L.; Morgan, B.; Mann, J. I. Br.
Med. J. 1990, 301, 584. (b) Mantell, G.; Burke, M. T.; Staggers, J.
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4.2.7. Compound 1g. Colourless liquid, 1.6 g (8%);
1
nmax(CHCl3) 3571 cmK1; H NMR (CDCl3, 300 MHz): d
7.21 (2H, d, JZ8.5 Hz, H-6 and H-2), 6.79 (2H, d, JZ
8.5 Hz, H-5 and H-3), 3.72 (3H, s, 40-OCH3), 1.74 (4H, m,
H-20 and H-20), 0.69 (6H, t, JZ7.3 Hz, H-30 and H-30); 13C
NMR (CDCl3, 75.4 MHz): d 158.0 (C-4), 137.9 (C-1), 126.6
(C-6 and C-2), 113.3 (C-5 and 3), 77.1 (C-10), 55.1
(4-OCH3), 34.8 (C-20 and C-20), 7.8 (C-30 and C-30);
HRMS (MCNa) m/z: 217.2595 (Calcd for C12H18O2Na:
217.2634).
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4.3. Synthesis of 1-(3,4,5-trimethoxy)phenyl-1-propa-
none (4a) and 1a from 3a
4. (a) Hamdouchi, C.; Warborsky, H. M. In Handbook of Grignard
Reagents; Silverman, G. S., Rakita, P. E., Eds.; Dekker: New
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A mixture of aryl alkyl carbinol (3a) (2.4 mmol) and
DDQ (4.8 mmol) in wet dioxane (30 mL) was stirred at
room temperature for 14 h. The precipitated DDQH2 was
filtered and the red coloured filtrate was evaporated and
subsequently chromatographed on silica gel (hexane/ethyl
acetate 7:3) to provide phenylpropanone 4a in 89%
whose spectral data was found matching with the
reported values. Further treatment of ketone 4a with
excess of ethylmagnesium bromide in ether and toluene
provided 1a in 78% yield.
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Vıcha, R.; Potacek, M. Tetrahedron 2005, 61, 83.
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1186. (b) Pathania, V.; Sharma, A.; Sinha, A. K. Helv. Chim.
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Acknowledgements
8. (a) Nishiguchi, I.; Sakai, M.; Maekawa, H.; Ohno, T.;
Yamamoto, Y.; Ishino, Y. Tetrahedron Lett. 2002, 43, 635.
(b) Sharma, A.; Joshi, B. P.; Sinha, A. K. Bull. Chem. Soc. Jpn.
2004, 77, 2231.
Two of us (A.S. and B.P.J.) are indebted to CSIR, Delhi for
the award of SRF. The authors gratefully acknowledge the
Director of I.H.B.T., Palampur for his kind cooperation and
encouragement.
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(b) Fu, P. P.; Harvey, R. G. Chem. Rev. 1978, 78, 317.