2-[2-(Ethenyloxy)ethoxy]-1H-isoindole-1,3(2H)-dione

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Part A: Synthesis of 2-(2-Vinyloxy-ethoxy)-isoindole-1,3-dione Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2H), 7.75 (m, 2H), 6.46 (dd, J=14.3, 6.7 Hz, 1H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Part A: Synthesis of 2-(2-Vinyloxy-ethoxy)-isoindole-1,3-dione Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2H), 7.75 (m, 2H), 6.46 (dd, J=14.3, 6.7 Hz, 1H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2 H), 7.75 (m, 2 H), 6.46 (dd, J=14.3, 6.7 Hz, 1 H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3 H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2 H), 7.75 (m, 2 H), 6.46 (dd, J=14.3, 6.7 Hz, 1 H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3 H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Part A: Synthesis of 2-(2-Vinyloxy-ethoxy)-isoindole-1,3-dione Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2H), 7.75 (m, 2H), 6.46 (dd, J=14.3, 6.7 Hz, 1H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol