2-(3-methylbut-2-enoxy)isoindole-1,3-dione

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

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

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

Procedure: Potassium carbonate (7.55 g, 54.6 mmol) was added to a solution of N-hydroxyphthalimide (13.93 g, 85.4 mmol) in 150 mL of DMSO to give a wine-red colored solution. 4-Bromo-2-methyl-2-butene (20 g, 134 mmol) was added to the solution dropwise and the reaction was stirred for 16 hours at room temperature. The reaction was poured into 600 mL of ice water to give a white crystalline solid. The crude crystalline product was filtered, washed with ice water, and air dried. The crystalline product was recrystallized from ethanol to give 15.7 g, m.p. 97°-98° C. to give a wine-red colored solution to give a white crystalline solid The crude crystalline product was filtered washed with ice water, and air dried The crystalline product was recrystallized from ethanol to give 15.7 g, m.p. 97°-98° C.

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

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

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

Procedure: 2-(3-Methyl-but-2-enyloxy)-isoindole-1,3-dione was dissolved in a t-butanol/THF/H2O solution (10 mL/3 mL/1 mL) and charged with N-methylmorpholine N-oxide (0.085 g, 0.73 mmol) and a catalytic amount of potassium osmate dihydrate. After stirring for 17 hours the reaction was diluted with a saturated solution of sodium metabisulfate and partitioned with ethyl acetate. The organic layer was washed twice with saturated solution of sodium metabisulfate, twice with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo affording 2-(2,3-dihydroxy-3-methyl-butoxy)-isoindole-1,3-dione as a clear oil, which was charged with dichloromethane (10 mL), 2,2-dimethoxypropane (0.12 mL, 0.75 mmol) and a catalytic amount of p-toluenesulfonic acid. After stirring for 17 hours, the reaction was concentrated in vacuo, and partitioned between ethyl acetate and water. The organic layer was washed twice with water, once with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo, affording 2-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethoxy)-isoindole-1,3-dione as a light brown solid (0.158 g, 77.1%): 1H NMR (400 MHz; DMSO-d6) δ 7.82 s, (4H), 4.12-4.26 (m, 2H), 4.04-4.07 (m, 1H), 1.22 (s, 9H) 1.17 (s, 3H), 0.97 s(3H). partitioned with ethyl acetate The organic layer was washed twice with saturated solution of sodium metabisulfate, twice with saturated sodium chloride solution collected dried over Na2SO4 filtered concentrated in vacuo

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

Procedure: 2-(3-Methyl-but-2-enyloxy)-isoindole-1,3-dione was dissolved in a t-butanol/THF/H2O solution (10 mL/3 mL/1 mL) and charged with N-methylmorpholine N-oxide (0.085 g, 0.73 mmol) and a catalytic amount of potassium osmate dihydrate. After stirring for 17 hours the reaction was diluted with a saturated solution of sodium metabisulfate and partitioned with ethyl acetate. The organic layer was washed twice with saturated solution of sodium metabisulfate, twice with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo affording 2-(2,3-dihydroxy-3-methyl-butoxy)-isoindole-1,3-dione as a clear oil, which was charged with dichloromethane (10 mL), 2,2-dimethoxypropane (0.12 mL, 0.75 mmol) and a catalytic amount of p-toluenesulfonic acid. After stirring for 17 hours, the reaction was concentrated in vacuo, and partitioned between ethyl acetate and water. The organic layer was washed twice with water, once with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo, affording 2-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethoxy)-isoindole-1,3-dione as a light brown solid (0.158 g, 77.1%): 1H NMR (400 MHz; DMSO-d6) δ 7.82 s, (4H), 4.12-4.26 (m, 2H), 4.04-4.07 (m, 1H), 1.22 (s, 9H) 1.17 (s, 3H), 0.97 s(3H). partitioned with ethyl acetate The organic layer was washed twice with saturated solution of sodium metabisulfate, twice with saturated sodium chloride solution collected dried over Na2SO4 filtered concentrated in vacuo

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of N-hydroxyphthalimide (Aldrich, 1.63 g, 10.0 mmol) in anhydrous ethanol (50 mL) was added 1-bromo-3-methyl-but-2-ene (Aldrich, 1.4 mL, 12.0 mmol) and potassium hydroxide (0.67 g, 12.0 mmol). After the reaction was allowed to stir at 50° C. for 4 hours, it was concentrated in vacuo and then dissolved in ethyl acetate and partitioned with water. The organic layer was washed twice with water, twice with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo, affording a white solid. The collected solid was purified via silica column in 10% methanol in dichloromethane to afford 2-(3-methyl-but-2-enyloxy)-isoindole-1,3-dione (0.53 g, 23%): 1H NMR (400 Mz; DMSO-d6) δ 7.81 (s, 4H), 5.38 (t, 1H, J=1.5), 4.57 (d, 2H, J=7.6) 1.67 (s, 3H), 1.62 (s, 3H); MS (APCI+)=232.0 it was concentrated in vacuo dissolved in ethyl acetate partitioned with water The organic layer was washed twice with water, twice with saturated sodium chloride solution collected dried over Na2SO4 filtered concentrated in vacuo affording a white solid The collected solid was purified via silica column in 10% methanol in dichloromethane

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

Procedure: Potassium carbonate (7.55 g, 54.6 mmol) was added to a solution of N-hydroxyphthalimide (13.93 g, 85.4 mmol) in 150 mL of DMSO to give a wine-red colored solution. 4-Bromo-2-methyl-2-butene (20 g, 134 mmol) was added to the solution dropwise and the reaction was stirred for 16 hours at room temperature. The reaction was poured into 600 mL of ice water to give a white crystalline solid. The crude crystalline product was filtered, washed with ice water, and air dried. The crystalline product was recrystallized from ethanol to give 15.7 g, m.p. 97°-98° C. to give a wine-red colored solution to give a white crystalline solid The crude crystalline product was filtered washed with ice water, and air dried The crystalline product was recrystallized from ethanol to give 15.7 g, m.p. 97°-98° C.

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

Procedure: Potassium carbonate (7.55 g, 54.6 mmol) was added to a solution of N-hydroxyphthalimide (13.93 g, 85.4 mmol) in 150 mL of DMSO to give a wine-red colored solution. 4-Bromo-2-methyl-2-butene (20 g, 134 mmol) was added to the solution dropwise and the reaction was stirred for 16 hours at room temperature. The reaction was poured into 600 mL of ice water to give a white crystalline solid. The crude crystalline product was filtered, washed with ice water, and air dried. The crystalline product was recrystallized from ethanol to give 15.7 g, mp 97°-98° C. to give a wine-red colored solution to give a white crystalline solid The crude crystalline product was filtered washed with ice water, and air dried The crystalline product was recrystallized from ethanol to give 15.7 g, mp 97°-98° C.

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

Procedure: Potassium carbonate (7.55 g, 54.6 mmol) was added to a solution of N-hydroxyphthalimide (13.93 g, 85.4 mmol) in 150 mL of DMSO to give a wine-red colored solution. 4-Bromo-2-methyl-2-butene (20 g, 134 mmol) was added to the solution dropwise and the reaction was stirred for 16 hours at room temperature. The reaction was poured into 600 mL of ice water to give a white crystalline solid. The crude crystalline product was filtered, washed with ice water, and air dried. The crystalline product was recrystallized from ethanol to give 15.7 g, mp 97°-98° C. to give a wine-red colored solution to give a white crystalline solid The crude crystalline product was filtered washed with ice water, and air dried The crystalline product was recrystallized from ethanol to give 15.7 g, mp 97°-98° C.

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

Procedure: 2-(3-Methyl-but-2-enyloxy)-isoindole-1,3-dione was dissolved in a t-butanol/THF/H2O solution (10 mL/3 mL/1 mL) and charged with N-methylmorpholine N-oxide (0.085 g, 0.73 mmol) and a catalytic amount of potassium osmate dihydrate. After stirring for 17 hours the reaction was diluted with a saturated solution of sodium metabisulfate and partitioned with ethyl acetate. The organic layer was washed twice with saturated solution of sodium metabisulfate, twice with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo affording 2-(2,3-dihydroxy-3-methyl-butoxy)-isoindole-1,3-dione as a clear oil, which was charged with dichloromethane (10 mL), 2,2-dimethoxypropane (0.12 mL, 0.75 mmol) and a catalytic amount of p-toluenesulfonic acid. After stirring for 17 hours, the reaction was concentrated in vacuo, and partitioned between ethyl acetate and water. The organic layer was washed twice with water, once with saturated sodium chloride solution, collected and dried over Na2SO4, filtered and concentrated in vacuo, affording 2-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethoxy)-isoindole-1,3-dione as a light brown solid (0.158 g, 77.1%): 1H NMR (400 MHz; DMSO-d6) δ 7.82 s, (4H), 4.12-4.26 (m, 2H), 4.04-4.07 (m, 1H), 1.22 (s, 9H), 1.17 (s, 3H), 0.97 s(3H). partitioned with ethyl acetate The organic layer was washed twice with saturated solution of sodium metabisulfate, twice with saturated sodium chloride solution collected dried over Na2SO4 filtered concentrated in vacuo