1-Ethynyl-4-pentylbenzene synthesis
- Product Name:1-Ethynyl-4-pentylbenzene
- CAS Number:79887-10-8
- Molecular formula:C13H16
- Molecular Weight:172.27
138220-08-3
79887-10-8
General procedure for the synthesis of 4-pentylphenylacetylene from trimethyl((4-pentylphenyl)ethynyl)silane: To a solution of tetrahydrofuran (THF, 6 mL) of trimethyl((4-pentylphenyl)ethynyl)silane (900 mg, 3.68 mmol) was added a solution of tetra-n-butylammonium fluoride (n-Bu4NF) in THF (1.0 M, 0.37 mL). The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the solvent was removed by rotary evaporator and the resulting residue was purified by silica gel column chromatography using hexane as eluent to afford 4-pentylphenylacetylene (615 mg, 97% yield) as a light yellow oil. The product was characterized by 1H NMR (CDCl3): δ 7.42 (d, J=8.3 Hz, 2H), 7.14 (d, J=8.3 Hz, 2H), 3.04 (s, 1H), 2.61 (t, J=7.8 Hz, 2H), 1.65-1.57 (m, 2H), 1.36-1.26 (m, 4H), 0.90 (t, J= 6.6Hz, 3H).
138220-08-3
2 suppliers
inquiry
79887-10-8
163 suppliers
$8.00/1g
Yield:79887-10-8 97%
Reaction Conditions:
with tetrabutyl ammonium fluoride in tetrahydrofuran at 20; for 1 h;
Steps:
4-Pentylphenylacetylene (5)
To a solution of 4 (900 mg, 3.68 mmol) in THF (6 mL) was added a solution of n-Bu4NF in THF (1.0 M, 0.37 mL). The resulting mixture was stirred at room temperature for 1 h. After evaporation of solvent, the residue was purified by column chromatography on silica gel eluted with hexane to give 5 (615 mg, 97% yield) as pale yellow oil. 1H NMR (CDCl3) δ 7.42 (d, J = 8.3 Hz,2H), 7.14 (d, J = 8.3 Hz, 2H), 3.04 (s, 1H), 2.61 (t, J = 7.8 Hz, 2H), 1.65-1.57 (m, 2H), 1.36-1.26 (m, 4H),0.90 (t, J = 6.6 Hz, 3H).
References:
Takaki, Yuta;Wakayama, Yutaka;Ishiguro, Yasushi;Hayakawa, Ryoma;Yamagishi, Masakazu;Okamoto, Toshihiro;Takeya, Jun;Yoza, Kenji;Kobayashi, Kenji [Chemistry Letters,2016,vol. 45,# 12,p. 1403 - 1405] Location in patent:supporting information
6853-57-2
55 suppliers
$45.70/1g
79887-10-8
163 suppliers
$8.00/1g
33228-44-3
104 suppliers
$15.00/1g
79887-10-8
163 suppliers
$8.00/1g
85017-60-3
56 suppliers
$30.00/1g
79887-10-8
163 suppliers
$8.00/1g