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

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Phthalimide, potassium salt (20.5 g, 0.11 mol) was suspended in dry DMF (100 mL). To the suspension was added 1-bromo-3-methyl-2-butene (14.8 g, 0.1 mol) with stirring. The reaction mixture was stirred under N2 at 45° C. for 24 h. TLC (silica gel, 30% ethyl acetate-hexane) showed one major UV-visible spot with Rf =0.65. DMF was removed under vacuum and the residue was taken up with water (200 mL) and extracted with ethyl acetate (3×150 mL). The extracts were combined and dried over Na2SO4. Evaporation of solvent gave the title product as a white solid. Yield: 21.0 g (98%). mp: 95°-97° C. MS: 233 (M+NH4)+, 216 (M+H)+. The reaction mixture was stirred under N2 at 45° C. for 24 h DMF was removed under vacuum extracted with ethyl acetate (3×150 mL) dried over Na2SO4 Evaporation of solvent

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 20 g of 1-bromo-3-methylbut-2-ene and 26.1 g of phthalimide are suspended in anhydrous DMF, and then the mixture is refluxed for 12 h with heating. After returning to RT, the reaction medium is filtered and then taken up with an aqueous solution saturated with NH4Cl. The aqueous phase is extracted with AcOEt, washed with a solution of NaCl, and then dried on magnesium sulfate and dry evaporated. The obtained solid is suspended in 100 mL of water and stirred. The precipitated product is filtered, rinsed with ether and then dried in the oven in vacuo at 65° C. 18.3 g (yield=63%) of 2-(3-methylbut-2-en-1-yl)-1H-isoindole-1,3-dione are obtained as a white powder used as such. the mixture is refluxed for 12 h with heating After returning to RT the reaction medium is filtered The aqueous phase is extracted with AcOEt washed with a solution of NaCl dried on magnesium sulfate dry evaporated The precipitated product is filtered rinsed with ether dried in the oven in vacuo at 65° C

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

実験手順: 20 g of 1-bromo-3-methylbut-2-ene and 26.1 g of phthalimide are suspended in anhydrous DMF, and then the mixture is refluxed for 12 h with heating. After returning to RT, the reaction medium is filtered and then taken up with an aqueous solution saturated with NH4Cl. The aqueous phase is extracted with AcOEt, washed with a solution of NaCl, and then dried on magnesium sulfate and dry evaporated. The obtained solid is suspended in 100 mL of water and stirred. The precipitated product is filtered, rinsed with ether and then dried in the oven in vacuo at 65° C. 18.3 g (yield=63%) of 2-(3-methylbut-2-en-1-yl)-1H-isoindole-1,3-dione are obtained as a white powder used as such. the mixture is refluxed for 12 h with heating After returning to RT the reaction medium is filtered The aqueous phase is extracted with AcOEt washed with a solution of NaCl dried on magnesium sulfate dry evaporated The precipitated product is filtered rinsed with ether dried in the oven in vacuo at 65° C

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

実験手順: 34.2 g of ethyl carbamate are put in the solution in the toluene, 22 mL of BF3.Et2O are added and heating is performed for 1 h 30 mins at 70° C. 11 g of 2-(3-methylbut-2-en-1-yl)-1H-isoindole-1,3-dione are added and heating with reflux is performed for 12 h. After returning to RT, the mixture is dry evaporated and then taken up in an H2O/AcOEt mixture. The organic phase is decanted, washed with a solution saturated with NaCl and then dried on magnesium sulfate. The crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 99/1). 5.12 g (yield=31%) of ethyl[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1,1-dimethylpropyl]-carbamate are obtained as a brown powder used as such. are added heating heating with reflux is performed for 12 h After returning to RT the mixture is dry evaporated The organic phase is decanted washed with a solution saturated with NaCl dried on magnesium sulfate The crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 99/1)

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

実験手順: 34.2 g of ethyl carbamate are put in the solution in the toluene, 22 mL of BF3.Et2O are added and heating is performed for 1 h 30 mins at 70° C. 11 g of 2-(3-methylbut-2-en-1-yl)-1H-isoindole-1,3-dione are added and heating with reflux is performed for 12 h. After returning to RT, the mixture is dry evaporated and then taken up in an H2O/AcOEt mixture. The organic phase is decanted, washed with a solution saturated with NaCl and then dried on magnesium sulfate. The crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 99/1). 5.12 g (yield=31%) of ethyl[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1,1-dimethylpropyl]-carbamate are obtained as a brown powder used as such. are added heating heating with reflux is performed for 12 h After returning to RT the mixture is dry evaporated The organic phase is decanted washed with a solution saturated with NaCl dried on magnesium sulfate The crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 99/1)

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

実験手順: Phthalimide, potassium salt (20.5 g, 0.11 mol) was suspended in dry DMF (100 mL). To the suspension was added 1-bromo-3-methyl-2-butene (14.8 g, 0.1 mol) with stirring. The reaction mixture was stirred under N2 at 45° C. for 24 h. TLC (silica gel, 30% ethyl acetate-hexane) showed one major UV-visible spot with Rf =0.65. DMF was removed under vacuum and the residue was taken up with water (200 mL) and extracted with ethyl acetate (3×150 mL). The extracts were combined and dried over Na2SO4. Evaporation of solvent gave the title product as a white solid. The reaction mixture was stirred under N2 at 45° C. for 24 h DMF was removed under vacuum extracted with ethyl acetate (3×150 mL) dried over Na2SO4 Evaporation of solvent

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

実験手順: Phthalimide, potassium salt (20.5 g, 0.11 mol) was suspended in dry DMF (100 mL). To the suspension was added 1-bromo-3-methyl-2-butene (14.8 g, 0.1 mol) with stirring. The reaction mixture was stirred under N2 at 45° C. for 24 h. TLC (silica gel, 30% ethyl acetate-hexane) showed one major UV-visible spot with Rf =0.65. DMF was removed under vacuum and the residue was taken up with water (200 mL) and extracted with ethyl acetate (3×150 mL). The extracts were combined and dried over Na2SO4. Evaporation of solvent gave the title product as a white solid. The reaction mixture was stirred under N2 at 45° C. for 24 h DMF was removed under vacuum extracted with ethyl acetate (3×150 mL) dried over Na2SO4 Evaporation of solvent

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

実験手順: Phthalimide, potassium salt (20.5 g, 0.11 mol) was suspended in dry DMF (100 mL). To the suspension was added 1-bromo-3-methyl-2-butene (14.8 g, 0.1 mol) with stirring. The reaction mixture was stirred under N2 at 45° C. for 24 h. TLC (silica gel, 30% ethyl acetate-hexane) showed one major UV-visible spot with Rf =0.65. DMF was removed under vacuum and the residue was taken up with water (200 mL) and extracted with ethyl acetate (3×150 mL). The extracts were combined and dried over Na2SO4. Evaporation of solvent gave the title product as a white solid. Yield: 21.0 g (98%). mp: 95°-97° C. MS: 233 (M+NH4)+, 216 (M+H)+. 1H NMR (CDCl3) ε 1.71 and 1.83 [s, 6H, C(CH3)2 ], 4.26 (d, J=6.6 Hz, 2H, CH2CH=), 5.30 (t, 1H, CH=), 7.67 to 7.86 (m, 4H, Aromatic-H). The reaction mixture was stirred under N2 at 45° C. for 24 h DMF was removed under vacuum extracted with ethyl acetate (3×150 mL) dried over Na2SO4 Evaporation of solvent

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

実験手順: Phthalimide, potassium salt (20.5 g, 0.11 mol) was suspended in dry DMF (100 mL). To the suspension was added 1-bromo-3-methyl-2-butene (14.8 g, 0.1 mol) with stirring. The reaction mixture was stirred under N2 at 45° C. for 24 h. TLC (silica gel, 30% ethyl acetate-hexane) showed one major UV-visible spot with Rf =0.65. DMF was removed under vacuum and the residue was taken up with water (200 mL) and extracted with ethyl acetate (3×150 mL). The extracts were combined and dried over Na2SO4. Evaporation of solvent gave the title product as a white solid. Yield: 21.0 g (98%). mp: 95°-97° C. MS: 233 (M+NH4)+, 216 (M+H)+. The reaction mixture was stirred under N2 at 45° C. for 24 h DMF was removed under vacuum extracted with ethyl acetate (3×150 mL) dried over Na2SO4 Evaporation of solvent