methyl 4-(4-chlorophenoxy)butanoate

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of methyl 4-(4-chlorophenoxy)butanoate (1.4 g, 6.13 mmol), aminoguanidine bicarbonate (2.08 g, 15.3 mmol), and pyridine (12 mL) was added to a 100 mL RBF with a magnetic stirring bar. The flask was fitted with a condenser, and heated to 125° C. using an oil bath. Progress of the reaction was monitored by analytical HPLC with UV detection at 215 nm. The mixture was heated for 20 hours, and an additional portion of aminoguanidine bicarbonate (0.60 g, 4.4 mmol) was added. After an additional 22 hours of heating, the reaction was complete. The reaction allowed to cool to ambient temperature, concentrated under reduced pressure and partitioned between ethyl acetate (50 mL) and water (20 mL). The aqueous layer was extracted once more with ethyl acetate (30 mL). The combined organic layers were washed with saturated aqueous NaCl (2×15 mL), dried (Na2SO4), filtered and concentrated. Dichloromethane (5 mL) was added and a precipitate that formed was isolated by filtration, rinsed with dichloromethane (5 mL), and then dried under reduced pressure to afford the title compound as a white powder (1.12 g, 72% yield). was added to a 100 mL RBF with a magnetic stirring bar The flask was fitted with a condenser The mixture was heated for 20 hours After an additional 22 hours of heating to cool to ambient temperature concentrated under reduced pressure partitioned between ethyl acetate (50 mL) and water (20 mL) The aqueous layer was extracted once more with ethyl acetate (30 mL) The combined organic layers were washed with saturated aqueous NaCl (2×15 mL) dried (Na2SO4) filtered concentrated Dichloromethane (5 mL) was added a precipitate that formed was isolated by filtration rinsed with dichloromethane (5 mL) dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of methyl 4-bromobutyrate (1.5 g, 8.29 mmol), 4-chlorophenol (1.17 g, 9.11 mmol), potassium carbonate (2.86 g, 20.7 mmol), and anhydrous N,N-dimethylformamide (5 mL) was added to a 25 mL RBF with a magnetic stirring bar. The mixture was allowed to stir at room temperature for 16 hours. Progress of the reaction was monitored by analytical HPLC with UV detection (Rt=6.5 min). The mixture was added to stirring ice/water (150 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated aqueous NaCl (2×30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using a gradient elution of 0-100% ethyl acetate in hexanes to afford the title compound as a clear oil (1.45 g, 76% yield). was added to a 25 mL RBF with a magnetic stirring bar The mixture was added extracted with ethyl acetate (2×30 mL) The combined organic layers were washed with saturated aqueous NaCl (2×30 mL) dried (Na2SO4) filtered concentrated under reduced pressure The crude material was purified by silica gel column chromatography a gradient elution of 0-100% ethyl acetate in hexanes