Boron trifluoride etherate → HCID 14652262, compound

Participants

Reaction Steps

To a solution of 6-diethylaminohex-4-ynal (50 g, 290 mmol) in methylene chloride (600 mL) was added 1,3-propanedithiol (30 mL, 290 mmol). The solution was stirred at room temperature for 1 hour and then cooled in an ice-bath. Boron trifluoride etherate (40 mL, 290 mmol) was added and the solution was stirred at room temperature overnight. The mixture was washed with water (150 mL), 10% potassium hydroxide solution (2×300 mL), brine (3×100 mL) and dried (MgSO4). Evaporation of the solvent afforded an oil which was Kugelrohr distilled (oven 120° C., 0.1 mm Hg) to give 20 g of product. The residue was chromatographed on basic alumina (activity I) eluting with methylene chloride and the oil was redistilled by Kugelrohr to afford 14 g (45%) of product. 1H NMR (CDCl3) δ: 1.14 (t, 6H), 1.80-1.90 (m, 1H), 1.91 (q, 2H), 2.05-2.15 (m, 1H), 2.43 (t, 2H), 2.52 (q, 4H), 2.81-2.90 (m, 4H), 3.39 (d, 2H), 4.17 (t, 1H) ppm.

Provenance & Evidence