2,4-HEPTADECADIYN-1-OL synthesis

5synthesis methods

Product Name:2,4-HEPTADECADIYN-1-OL
CAS Number:64034-03-3
Molecular formula:C17H28O
Molecular Weight:248.4

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Yield:64034-03-3 73%

Reaction Conditions:

with hydroxylamine hydrochloride;ethylamine;copper(l) chloride in methanol;water; for 20 h;Cadiot-Chodkiewicz Coupling;

Steps:

4.2.7 Heptadeca-2,4-diyn-1-ol (14)

To a stirred solution of propargyl alcohol (23mg, 0.42mmol), ethylamine (0.15mL of 70% w/w solution in water) and 1-bromo-1-tetradecyne 12 (100mg, 0.366mmol) in MeOH (5mL), was added freshly prepared CuCl (1mg, 0.01mmol). After the reaction mixture turned to a yellowish green color, hydroxylamine hydrochloride (7mg, 0.1mmol) was added, inducing an immediate change of the color which became yellow. The reaction was monitored by TLC (pentane/Et₂O 10:1) and reached completion after 20h. Then, the mixture was filtered through a short pad of Celite, and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in EtOAc, washed with water and saturated brine. The organic layer was dried over Na₂SO₄ and concentrated under reduced pressure. The residue was purified by silica gel (pentane/Et₂O 10:1) to give 14 as a white solid 76mg (73%). The obtained physical data were in agreement with literature.²⁰

References:

Listunov, Dymytrii;Saffon-Merceron, Nathalie;Joly, Etienne;Fabing, Isabelle;Génisson, Yves;Maraval, Valérie;Chauvin, Remi [Tetrahedron,2016,vol. 72,# 42,p. 6697 - 6704] Location in patent:supporting information