E
Z. Chen et al.
Letter
Synlett
References and Notes
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(24) Ethyl 3-Phenylpropiolate (3a); Typical Procedure: A mixture
of phenylpropiolic acid (1a; 0.2 mmol) and GO (50 wt%, calcd
based on the mass of acid) in EtOH (1 mL) was placed in a test
tube equipped with a magnetic stirring bar. The mixture was
stirred and heated at 100 °C for 24 h. Upon completion of the
reaction, GO was filtered, the solvent was removed, and the
residue was separated by column chromatography (petroleum
ether/ethyl acetate, 10:1) to give 1a (34 mg, 98%) as a yellow
liquid. 1H NMR (400 MHz, CDCl3): δ = 7.63–7.54 (m, 2 H), 7.49–
7.41 (m, 1 H), 7.41–7.32 (m, 2 H), 4.29 (q, J = 7.2 Hz, 2 H), 1.35 (t,
J = 7.2 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ = 154.0, 132.9,
130.6, 128.5, 119.6, 86.0, 80.7, 62.1, 14.0. MS (EI): m/z = 174,
146, 129, 118, 102, 89, 75, 63, 51, 39, 29.
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–E