Ethylene Glycol → HCID 86623937, compound

Participants

Reaction Conditions

Reaction Steps

Cuprous iodide (12 mg) and anhydrous potassium carbonate (0.33 g, 2.4 mmol) were placed in a tube (15×2 cm) equipped with a magnetic stirring bar, and 6-ethylmercapto-8-mercapto octanoic acid (Compound (H)) (0.19 g, 0.8 mmol) in 2-methyl-2-butanol (2 mL) was added. The tube was closed with a septum cap and flushed with argon. Ethylene glycol (100 mg, 90 μL, 1.6 mmol) was added via a syringe followed by iodobenzene (164 mg, 90 μL, 0.8 mmol,). The tube was flushed again with argon, then sealed with parafilm and stirred at 95° C. for 38 h. The mixture was cooled to room temperature, and water (15 mL) was added. The pH of the suspension was adjusted to 2 with 2.0 M hydrochloric acid. The mixture was extracted with chloroform (3×10 mL). The combined extracts were dried over magnesium sulfate and filtered, and the solvent was evaporated to yield a yellow oil weighing 0.25 g. TLC (CHCl3—CH3OH—HOAc 100:10:1) and showing a major spot with Rf=0.45, a minor spot with Rf=0.39 and several minor spots. The crude product in chloroform (0.5 mL) was applied to a column (12×2.2 cm) with silica gel 60 (20 g) packed in CHCl3—CH3OH—HOAc (100:5:1). The column was eluted with CHCl3—CH3OH—HOAc (100:10:1). Fractions of 4-5 mL were collected at a flow rate of 0.5 mL/min. The product was collected in fractions 7-10: colorless oil weighing 140 mg. TLC Rf=0.45 (silica gel; CHCl3—CH3OH—HOAc, 100:10:1); 1H-NMR (CDCl3): δ 7.1-7.4 (m, 5H), 3.08 (td, 2H), 2.6-2.8 (m, 1H), 2.48 (q, 2H), 2.35 (t, 2H), 1.3-1.9 (m, 8H), 1.22 (t, 3H); MS (ESI (−)): 311 (M-1).

Provenance & Evidence