Ammonium Chloride → HCID 19849489, compound

Participants

Reaction Conditions

Reaction Steps

3.99 ml (2.15 g, 0.016 mol) of a 4.05N solution of ethylmagnesium bromide in ether was added dropwise under argon to a solution of 2.879 (0.0161 mol) of hexa-2,5-diyn-1-ol tetrahydropyranyl ether [D. Van der Steen et al, Recueil 82, 1015 (1963)] in 30 ml of tetrahydrofuran maintained at -20° C. After the addition was finished, the reactionmixture was stirred for 2 hours further at -20° C. Then, 52.8 mg (0.53 mmol) of cuprous chloride was added. The mixture was stirred for 20 additional minutes, warmed to room temperature and 2.2 g (0.008 mol) of 1-iodo-4-phenoxybut-2-yne was added. The reaction mixture was then stirredat room temperature for 3 hours, poured into 50 ml of saturated ammonium chloride solution and extracted with ether (3×50 ml). The combined extracts were dried over sodium sulfate and the solvent removed by evaporation in vacuo. The residue was purified by column chromatography on80 g of silica gel, using hexane:ether (90:10) as eluant thus obtaining thetetrahydropyranyl ether of 10-phenoxydeca-2,5,8-triyn-1-ol, as an oil. Thisproduct was stored in dry ice.

Provenance & Evidence