5530
S. S. Palimkar et al. / Tetrahedron Letters 47 (2006) 5527–5530
chromatography using ethyl acetate/petroleum ether as
Acknowledgements
eluent to afford the desired product.
Analytical data for some representative compounds.
S.S.P. thanks the CSIR, New Delhi, for the award of a
Research Fellowship.
1
-Phenyl-3-p-tolylprop-2-yn-1-one 3b. Colourless solid; mp
À1
1
6
0–61 °C; IR (film, cm ) 3018, 2196, 1637, 1215, 700; H
): d 2.41 (s, 3H), 7.23 (d, 2H,
J = 8.08 Hz), 7.47–7.67 (m, 5H), 8.23 (dt, 2H, J = 6.96 Hz,
NMR (200 MHz, CDCl
3
1
3
References and notes
3
1.64 Hz); C NMR (50 Hz, CDCl ): d 21.7, 86.7, 93.7,
1
16.9, 128.5, 129.4, 133.0, 133.9, 136.9, 141.5, 177.9. Anal.
1
2
. (a) Faweett, C. H.; Firu, R. D.; Spencer, D. M. Physiol.
Plant Pathol. 1971, 1, 163; (b) Imai, K. J. Pharm. Soc. 1956,
Calcd for C16
5.43.
H12O: C, 87.25; H, 5.49. Found: C, 87.15; H,
76, 405; (c) Drews, S. E.; Libenberg, R. W. EP 130 829,
3-(4-(Trifluoromethyl)phenyl)-1-o-tolylprop-2-yn-1-one 3h.
Colourless solid; mp 72 °C; IR (film, cm ) 2926, 2160,
1650, 1303, 757; H NMR (200 MHz, CDCl
À1
January 1985; Chem. Abstr. 1985, 103, 22381x.
. (a) Reid, W.; Koenig, E. Justus Leibig Ann. Chem. 1972, 24,
1
): d 2.68 (s,
3
7
55; (b) Hojo, M.; Tomita, K.; Hosomi, A. Tetrahedron
3H), 7.26–7.54 (m, 3H), 7.67 (d, 2H, J = 8.48 Hz), 7.77 (d,
13
Lett. 1993, 34, 485; (c) Arcadi, A.; Marenelli, F.; Rossi, E.
Tetrahedron 1999, 55, 13233; (d) Kelin, A. V.; Sromek, A.
W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074; (e)
Jeevnandan, A.; Narkunan, K.; Ling, Y. J. Org. Chem.
2H, J = 8.21 Hz), 8.29 (d, 1H, J = 7.50 Hz); C NMR
(50 Hz, CDCl ): d 21.9, 89.2, 89.5, 120.7, 124.2, 125.6,
125.9, 131.7, 132.3, 132.9, 133.2, 135.3, 140.7, 179.2. Anal.
3
Calcd for C17
H, 3.71.
11 3
H F O: C, 70.83; H, 3.85. Found: C, 70.81;
2001, 66, 6014; (f) Grotjahn, D. B.; Van, S.; Combs, D.;
Lev, D. A.; Schneider, C.; Rideout, M.; Meyer, C.;
Hernandez, G.; Mejorado, L. J. Org. Chem. 2002, 67,
1-(4-Chlorophenyl)-3-p-tolylprop-2-yn-1-one 3j. Colourless
À1
solid; mp 117–119 °C; IR (film, cm ) 3019, 2196, 1636,
1
9
3
200; (g) Karpov, A. S.; Muller, T. J. Org. Lett. 2003, 5,
451.
1215, 668; H NMR (200 MHz, CDCl
3
): d 2.40 (s, 3H), 7.23
(d, 2H, J = 8.09 Hz), 7.48 (d, 2H, J = 8.65 Hz), 7.57 (d, 2H,
13
3
. Gholap, A. R.; Venkatesan, K.; Pasricha, R.; Daniel, T.;
Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2005, 70,
J = 8.07 Hz) 8.15 (d, 2H, J = 8.71 Hz); C NMR (50 Hz,
CDCl ): d 21.7, 86.4, 94.3, 116.7, 128.9, 129.5, 130.7, 133.1,
3
4
869.
. Tohda, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1977,
77.
. Alonso, D. A.; Najera, C.; Pacheco, M. C. J. Org. Chem.
004, 69, 1615.
135.3, 140.5, 141.7, 176.6. Anal. Calcd for C16
75.45; H, 4.35. Found: C, 75.78; H, 4.31.
1-(4-Chlorophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one 3k.
H11ClO: C,
4
5
7
À1
Colourless solid; mp 116–117 °C; IR (film, cm ) 3019,
1
2
2192, 1635, 1215, 758; H NMR (200 MHz, CDCl
3
): d 3.79
6
7
. Chen, L.; Li, C. J. Org. Lett. 2004, 6, 3151.
(s, 3H), 6.86 (dt, 2H, J = 9.07, 1.94 Hz), 7.41 (dt, 2H,
. Cox, R. J.; Ritson, D. J.; Dane, T. A.; Berge, J.; Charmant,
J. P. H.; Kantacha, A. Chem. Commun. 2005, 1037.
. General procedure for ynone synthesis: A mixture of acid
J = 8.75, 1.89 Hz), 7.56 (dt, 2H, J = 8.91, 2.11 Hz), 8.07
1
3
(dt, 2H, J = 8.75, 2.05 Hz); C NMR (50 Hz, CDCl
3
): d
8
55.3, 86.5, 94.8, 111.5, 114.4, 128.8, 130.7, 135.1, 135.3,
chloride (1 mmol), terminal alkyne (1 mmol), Et
3
N
140.3, 161.8, 176.5. Anal. Calcd for C16
H, 4.10. Found: C, 70.84; H, 4.42.
H11ClO : C, 70.99;
2
(
1 mmol) and Pd(OAc) (0.2 mol%) was stirred at room
2
temperature for 10 min under an atmosphere of argon.
Completion of the reaction was monitored by TLC. After
completion, the reaction mixture was extracted with ethyl
acetate. The organic layer was washed with water to
dissolve the amine hydrochloride formed. The organic layer
was then separated, dried over magnesium sulfate, filtered
and concentrated under vacuum to obtain the crude
product. The crude product was further purified by column
3-Phenyl-1-(thiophen-2-yl)prop-2-yn-1-one 3o. Colourless
À1
solid; mp 53–54 °C; IR (film, cm ) 3016, 2200, 1618,
1
1411, 756; H NMR (200 MHz, CDCl
): d 7.17–7.21
3
(m, 1H), 7.37–7.53 (m, 3H), 7.64–7.74 (m, 3H), 8.01 (dd,
1
3
1H, J = 2.96, 1.31 Hz); C NMR (50 Hz, CDCl
3
): d 86.4,
91.6, 119.7, 128.3, 128.6, 130.7, 132.8, 135.2, 144.8, 169.6.
Anal. Calcd for C13
73.48; H, 4.16.
H OS: C, 73.56; H, 3.80. Found: C,
8