2,5-Octadiyn-1-ol synthesis

7synthesis methods

Product Name:2,5-Octadiyn-1-ol
CAS Number:35378-76-8
Molecular formula:C8H10O
Molecular Weight:122.16

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Yield:35378-76-8 98%

Reaction Conditions:

with copper(l) iodide;tetra-(n-butyl)ammonium iodide;potassium carbonate in N,N-dimethyl-formamide at 20; for 16 h;

Steps:

1 Preparation of Compound of Formula 3 (Octa-2, 5-dryn-l-ol:)

To a stirred solution of potassium carbonate (47.8 g, 0.34 mol), Cul (43.9 g, 0.23 mol), and TBAI (85.30 g, 0.23 mol) in DMF (440 mL) cooled to 0 °C, propargyl alcohol (15.52 g, 0.27 mol) was added portion wise at room temperature followed by compound represented by Formula 2 (55 g, 0.23 mol) and the reaction mixture was stirred at room temperature for 16 h. After completion of starting materials, the reaction mixture was cooled to 0 °C and diluted with cold water, ethyl acetate (300 mL x 2), filtered through celite bed and washed with ethyl acetate. The combined organic extracts were washed with cold water (200 mL x 2), brine (100 mL x 2) and dried over anhydrous Na₂S0₄. Solvent was evaporated under reduced pressure to obtain the crude product which was purified by column chromatography (100-200 mesh silica gel, 20 % EtOAc in hexane) to furnish octa-2, 5-diyn-l-ol (55 g, 98 %) as a light red liquid.

References:

WO2013/71411,2013,A1 Location in patent:Page/Page column 18