methyl 4-oxohexanoate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a stirring solution of 4.05 g (28 mmol) of methyl 4-oxohexanoate (16), prepared as described above in Example 16, in 200 mL of toluene and 0.53 g (2.8 mmol) of tosyl acid was added 5.59 g (90 mmol) of ethylene glycol. After refluxing for 2 hours using a Dean-Stark trap, the solvent was removed under vacuum. The resulting orange oil was dissolved in 200 mL of EtOAc. The EtOAc was then washed with 2×200 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated in vacuo to yield 4.96 g (94%) of methyl 2-ethyl-1,3-dioxolane-2-propanoate (17), which was employed immediately in Example 18 below. After refluxing for 2 hours the solvent was removed under vacuum The resulting orange oil was dissolved in 200 mL of EtOAc The EtOAc was then washed with 2×200 mL of H2O The organic layer was then dried over Na2SO4 anhydrous filtered concentrated in vacuo

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

Procedure: To a stirring solution of 4.05 g (28 mmol) of methyl 4-oxohexanoate (16), prepared as described above in Example 16, in 200 mL of toluene and 0.53 g (2.8 mmol) of tosyl acid was added 5.59 g (90 mmol) of ethylene glycol. After refluxing for 2 hours using a Dean-Stark trap, the solvent was removed under vacuum. The resulting orange oil was dissolved in 200 mL of EtOAc. The EtOAc was then washed with 2×200 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated in vacuo to yield 4.96 g (94%) of methyl 2-ethyl-1,3-dioxolane-2-propanoate (17), which was employed immediately in Example 18 below. After refluxing for 2 hours the solvent was removed under vacuum The resulting orange oil was dissolved in 200 mL of EtOAc The EtOAc was then washed with 2×200 mL of H2O The organic layer was then dried over Na2SO4 anhydrous filtered concentrated in vacuo

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

Procedure: To a stirring suspension of 8.15 g (25 mmol) of Cs2CO3 in DMF was added 5.79 g (44 mmol) of 4-oxohexanoic acid. After 5 minutes, 6.81 g (48 mmol) of iodomethane was added. The reaction mixture was stirred at ambient temperature for 16 hours. To the reaction was then added 250 mL of EtOAc and 250 mL of H2O. The layers were separated, and the organic layer was washed with 3×250 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated under vacuum. The yield of methyl 4-oxohexanoate (16) was 4.15 g (65%), which was employed in Example 17 below. The layers were separated the organic layer was washed with 3×250 mL of H2O The organic layer was then dried over Na2SO4 anhydrous filtered concentrated under vacuum

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

Procedure: To a stirring suspension of 8.15 g (25 mmol) of Cs2CO3 in DMF was added 5.79 g (44 mmol) of 4-oxohexanoic acid. After 5 minutes, 6.81 g (48 mmol) of iodomethane was added. The reaction mixture was stirred at ambient temperature for 16 hours. To the reaction was then added 250 mL of EtOAc and 250 mL of H2O. The layers were separated, and the organic layer was washed with 3×250 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated under vacuum. The yield of methyl 4-oxohexanoate (16) was 4.15 g (65%), which was employed in Example 17 below. The layers were separated the organic layer was washed with 3×250 mL of H2O The organic layer was then dried over Na2SO4 anhydrous filtered concentrated under vacuum

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

Procedure: Following the method of Example 2, but using 1-[1-(chlorophenyl)methyl-1-(3,5-dichlorophenyl) hydrazine hydrochloride and methyl 4-oxohexanoate as the starting materials, in t-butanol as solvent, the title compound was prepared.

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

Procedure: To a stirring solution of 4.05 g (28 mmol) of methyl 4-oxohexanoate (16), prepared as described above in Example 16, in 200 mL of toluene and 0.53 g (2.8 mmol) of tosyl acid was added 5.59 g (90 mmol) of ethylene glycol. After refluxing for 2 hours using a Dean-Stark trap, the solvent was removed under vacuum. The resulting orange oil was dissolved in 200 mL of EtOAc. The EtOAc was then washed with 2×200 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated in vacuo to yield 4.96 g (94%) of methyl 2-ethyl-1,3-dioxolane-2-propanoate (17), which was employed immediately in Example 18 below. After refluxing for 2 hours the solvent was removed under vacuum The resulting orange oil was dissolved in 200 mL of EtOAc The EtOAc was then washed with 2×200 mL of H2O The organic layer was then dried over Na2SO4 anhydrous filtered concentrated in vacuo

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

Procedure: To a stirring suspension of 8.15 g (25 mmol) of Cs2CO3 in DMF was added 5.79 g (44 mmol) of 4-oxohexanoic acid. After 5 minutes, 6.81 g (48 mmol) of iodomethane was added. The reaction mixture was stirred at ambient temperature for 16 hours. To the reaction was then added 250 mL of EtOAc and 250 mL of H2O. The layers were separated, and the organic layer was washed with 3×250 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated under vacuum. The yield of methyl 4-oxohexanoate (16) was 4.15 g (65%), which was employed in Example 17 below. The layers were separated the organic layer was washed with 3×250 mL of H2O The organic layer was then dried over Na2SO4 anhydrous filtered concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a stirring solution of 4.05 g (28 mmol) of methyl 4-oxohexanoate (16), prepared as described above in Example 16, in 200 mL of toluene and 0.53 g (2.8 mmol) of tosyl acid was added 5.59 g (90 mmol) of ethylene glycol. After refluxing for 2 hours using a Dean-Stark trap, the solvent was removed under vacuum. The resulting orange oil was dissolved in 200 mL of EtoAc. The EtoAc was then washed with 2×200 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated in vacuo to yield 4.96 g (94%) of methyl 2-ethyl-1,3-dioxolane-2-propanoate (17), which was employed immediately in Example 18 below. After refluxing for 2 hours the solvent was removed under vacuum The resulting orange oil was dissolved in 200 mL of EtoAc The EtoAc was then washed with 2×200 mL of H2O The organic layer was then dried over Na2SO4 anhydrous filtered concentrated in vacuo

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

Procedure: To a stirring suspension of 8.15 g (25 mmol) of Cs2CO3 in DMF was added 5.79 g (44 mmol) of 4-oxohexanoic acid. After 5 minutes, 6.81 g (48 mmol) of iodomethane was added. The reaction mixture was stirred at ambient temperature for 16 hours. To the reaction was then added 250 mL of EtOAc and 250 mL of H2O. The layers were separated, and the organic layer was washed with 3×250 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated under vacuum. The yield of methyl 4-oxohexanoate (16) was 4.15 g (65%), which was employed in Example 17 below. The layers were separated the organic layer was washed with 3×250 mL of H2O The organic layer was then dried over Na2SO4 anhydrous filtered concentrated under vacuum

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

Procedure: To a stirring solution of 4.05 g (28 mmol) of methyl 4-oxohexanoate (16), prepared as described above in Example 16, in 200 mL of toluene and 0.53 g (2.8 mmol) of tosyl acid was added 5.59 g (90 mmol) of ethylene glycol. After refluxing for 2 hours using a Dean-Stark trap, the solvent was removed under vacuum. The resulting orange oil was dissolved in 200 mL of EtoAc. The EtoAc was then washed with 2×200 mL of H2O. The organic layer was then dried over Na2S04 anhydrous, filtered, and concentrated in vacuo to yield 4.96 g (94%) of methyl 2-ethyl-1,3-dioxolane-2-propanoate (17), which was employed immediately in Example 18 below. After refluxing for 2 hours the solvent was removed under vacuum The resulting orange oil was dissolved in 200 mL of EtoAc The EtoAc was then washed with 2×200 mL of H2O The organic layer was then dried over Na2S04 anhydrous, filtered concentrated in vacuo