Ammonium Chloride → (E)-4-methyl-3,5-dioxa-7-octadecen-9,12-diyne

Participants

Reaction Steps

A solution of ethyl magnesium bromide in tetrahydrofuran (47 mL, 1.17 M) was treated dropwise with a solution of (E)-4-methyl-3,5-dioxa-7-decen-9-yne (7.7 g) in tetrahydrofuran (10 mL). After complete addition, the mixture was heated at 60° for 45 min, cooled to room temperature, treated with anhydrous cuprous chloride (0.35 g, dried at 145° at 0.05 mmHg for 16 hours) and stirred for 10 min. The 1-bromo-2-octyne (7.23 g) in tetrahydrofuran (10 mL) was added dropwise to the above mixture (mild exothermic reaction) and after complete addition the resulting mixture was heated for 45 min at 60° C. After this time, the contents were cooled to room temperature, poured onto saturated aqueous ammonium chloride solution and extracted with ether. The combined ether extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by liquid chromatography (two columns, 3% by volume ethyl acetate in 97% by volume hexane) to yield the product (E)-4-methyl-3,5-dioxa-7-octadecen-9,12-diyne

Provenance & Evidence