E
L. Gao, Z. Li
Letter
Synlett
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(23) 1-Arylprop-1-ynes (2a–x); General Procedure
A mixture of the appropriate aromatic aldehyde p-tosylhydra-
zone (1 mmol), calcium carbide (3 mmol, 0.20 g for 98% purity),
tBuOK (2 mmol, 0.22 g), CuI (1.2 mmol, 0.23 g), and H2O (4
mmol, 0.07 mL) in DMF (4 mL) was stirred at 90 °C for 6 h.
When the reaction was complete, the mixture was filtered to
remove solids and the liquor was extracted with EtOAc (3 × 10
mL) then washed with sat. brine (3 × 10 mL). The resulting
organic phase was dried (Na2SO4) and concentrated under
reduced pressure. The residue was purified by column chroma-
tography (silica gel, PE).
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1-Phenylprop-1-yne (2a)
Colorless liquid; yield: 83.6 mg (72%). 1H NMR (600 MHz,
CDCl3): = 7.39 (dd, J = 7.7, 2.0 Hz, 2 H), 7.30–7.24 (m, 3 H), 2.05
(s, 3 H). 13C NMR (151 MHz, CDCl3): = 131.46, 128.17, 127.48,
124.01, 85.76, 79.71, 4.29. HRMS: m/z [M + H]+ calcd for C9H9:
117.0699; found: 117.0698.
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(2-Prop-1-yn-1-ylphenyl)amine (2h)
Brown liquid; yield: 87.1 mg (66%). 1H NMR (600 MHz, CDCl3):
= 7.24 (d, J = 7.8 Hz, 1 H), 7.10–7.06 (m, 1 H), 6.75 (d, J = 8.1 Hz,
1 H), 6.70 (t, J = 7.5 Hz, 1 H), 2.11 (s, 3 H). 13C NMR (151 MHz,
CDCl3): = 146.97, 132.01, 128.77, 118.29, 114.52, 109.40,
91.18, 76.06, 4.53. HRMS: m/z [M + H]+ calcd for C9H10N:
132.0808; found: 132.0808.
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© 2019. Thieme. All rights reserved. — Synlett 2019, 30, A–E