HCID 19097835, compound → HCID 19097837, compound

Participants

Reaction Steps

Following the procedure described in Singh, A. & Schnur, J. M., Synthetic Comm. 16, 847 (1986), 1-iodo-4-oxa-tetradecyne (10 mmol) was coupled with 9-oxa-11-dodecynoic acid (1.98 g, 10 mmol) to produce 1.2 g 9,16-dioxa-hexacosa-11,13-diynoic acid (31% yield). The 9-oxa-11-dodecynoic acid was dissolved in aqueous KOH solution (1.1 mol eq.). CuCl (0.25 mol eq.) in ethylamine (70% aq. solution) was added, followed by 15 mg±5 mg hydroxyl amine hydrochloride NH2OH.HCl crystals. To this solution (yellow) was then added, in small portions, the 1-iodo-4-oxa-tetradecyne dissolved in 10 ml of CH3OH--CH3CH2OCH2CH3 (1:1). On addition of 1-iodo-4-oxa-tetradecyne the reaction mixture turned blue, and then yellow on addition of a few drops of 10% aqueous NH2OH.HCl solution.

Provenance & Evidence