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3
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Experimental
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Typical procedure for the synthesis of N-vinylbenzamides
A THF solution of LDA (2 M, 1.2 mL, 2.4 mmol) was added
to the stirred solution of 2-phenyl-2-oxazolines (2 mmol) in THF
(10 mL) at room temperature under an argon atmosphere. After
the resulting mixture was stirred for a given period of time, RX
(2 mmol) and DMF (5 mL) were added. The reaction mixture
was stirred overnight. The solvent was removed under reduced
pressure, and the residue was purified by column
chromatography on silica using ethyl acetate/petroleum ether
(v/v=1:8) as the eluent to give the corresponding N-
vinylbenzamides.
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Gram scale synthesis
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A THF solution of LDA (2 M, 4.8 mL, 9.6 mmol) was added
to the stirred solution of 2-phenyl-2-oxazoline (1.18 g, 8 mmol)
in THF (40 mL) at room temperature under an argon atmosphere.
After the resulting mixture was stirred for 0.5 h, allyl bromide
(0.59 mL, 8 mmol) or propargyl bromide (0.60 mL, 8 mmol) and
DMF (15 mL) were added, respectively. The reaction mixture
was stirred overnight. The solvent was removed under reduced
pressure, and the residue was purified by column
chromatography on silica using ethyl acetate/petroleum ether
(v/v=1:8) as the eluent to give 8 or 10. Yield: 1.25 g (83%) for 8
and 1.12 g (75%) for 10, respectively.
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7925.
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2007;129:2259–2268.
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2009;74:2231–2233.
J Org Chem.
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Acknowledgments
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21. (a) Zhang X, Xu X–M, Zhao L, You J, Zhu J, Wang M–X. Tetrahedron
Lett. 2015;56:3898–3901;
This work is supported by the National Natural Science
Foundation of China (No. 21372124).
(b) García A, Rodríguez D, Castedo L, SaáC, Domínguez D. Tetrahedron
Lett. 2001;42:1903–1905.
Supplementary material
22. (a) Ishibashi H, Ohata K, Niihara M, Sato T, Ikeda M. J Chem Soc Perkin
Trans 1. 2000;547−553;
Experiment details, spectroscopic data, 1H and 13C NMR
(b) Couture A, Lablache-Comber RDA. Tetrahedron. 1984;40:1835−1844;
(c) Krompiec S, Pigulla M, Kuźnik N, Krompiec M, Marciniec B,
Chadyniak D, Kasperczyk J. J Mol Catal A: Chem. 2005;225:91–101.
1
spectra of compounds 1-37 as well as H NMR spectra for the
reaction of 2-phenyl-2-oxazoline with LDA at 0oC under different
reaction times are provided.
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