Hydrochloric Acid → HCID 57817098, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Compound 8 (0.25 mmol) in 10 mL of THF was added 0.55 mmol of KOH. The solution was heated to reflux and was stirred for 15 mm, poured into 10 mL of 1 N HCl and extracted with methylene chloride (4×50 mL). The organic phase was washed with brine, dried with Mg2SO4, filtered through a plug of activated charcoal and silica gel, and evaporated under reduced pressure. The resulting oil was dissolved in 15 mL of dry THF under a dry nitrogen atmosphere and ethylene carbonate dissolved in dry THF (80 mg, 1 mmol) was added and the solution cooled to 0° C. To this solution with rapid stirring was added dry pyridine (0.5 mmol). The solution was stirred for, 1 hour and then poured into 10 mL of 1 N HCl and extracted with methylene chloride (4×50 mL). The organic phase was washed with brine, dried with Mg2SO4, filtered through a plug of activated charcoal and silica gel, and evaporated under reduced pressure. Overall yield: ˜0.08 mmol (35%). 1H NMR (CDCl3, TMS) δ, 7.629 (m, J 7.55 Hz, 2H), 7.41-7.27 (m, 3H), 7.18 (t, 1H), 6.91 (s, 1H) 6.87 (m, 1H), 6.77 (m, 1H), 6.07 (s, 1H), 4.15-4.05 (m, 2H), 4.03-3.96 (m, 4H), 3.84 (m, 2H), 2.28 (d, 1H), 2.08 (d, 1H).

Provenance & Evidence