3a,4,7,7a-tetrahydro-2-benzofuran-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:

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

Procedure: A mixture of 9.0 g of 19A, 6.8 g of THPA and 100 mL of glacial acetic acid was heated at reflux temperature for 4 hours. The resulting mixture was cooled to room temperature, poured into 450 mL of water and extracted with ether. The extract phase was washed with water, dried (Na2SO4), and filtered, and the solvent was evaporated from the filtrate. The residue was flash-chromatographed on silica gel, with a 15:85 v:v mixture of ethyl acetate and hexane as eluent, to give N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide (19B), as an orange oil. was heated at reflux temperature for 4 hours extracted with ether The extract phase was washed with water dried (Na2SO4) filtered the solvent was evaporated from the filtrate The residue was flash-chromatographed on silica gel, with a 15:85 v v mixture of ethyl acetate and hexane as eluent

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

Procedure: A mixture of 4.4 g of THPA, 5.3 g of 3B and 60 mL of glacial acetic acid was refluxed for 1 hour, then poured into 300 mL of ice water. The resulting mixture was allowed to stand for 10 minutes, then filtered. The collected solid was washed with cold water, dried under reduced pressure and recrystallized from ethyl acetate/hexane, to give N-(3-(allyloxy)-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide (3C), as yellow crystals, m.p.: 118.5°-120° C. was refluxed for 1 hour filtered The collected solid was washed with cold water dried under reduced pressure recrystallized from ethyl acetate/hexane

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

Procedure: 4,7,3a,7a-Tetrahydroisobenzofuran-1,3-dione is added to a solution sodium borohydride in 2-propanol at room temperature and reacted to obtain 4,7,3a,7a-tetrahydroisobenzofuran-1(3H)-one. reacted

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Octadecylamine (5.31 g) was added to 4,7,3a,7a-tetrahydroisobenzofuran-1,3-dione (3.00 g). After being stirred for 2 hours at 110° C., the reaction mixture was purified by silica gel column chromatography (silica gel 80 g, chloroform), thereby yielding the entitled compound (7.85 g) as yellow crystals. the reaction mixture was purified by silica gel column chromatography (silica gel 80 g, chloroform)

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

Procedure: A mixture of 9.0 g of 19A, 6.8 g of THPA and 100 mL of glacial acetic acid was heated at reflux temperature for 4 hours. The resulting mixture was cooled to room temperature, poured into 450 mL of water and extracted with ether. The extract phase was washed with water, dried (Na2SO4), and filtered, and the solvent was evaporated from the filtrate. The residue was flash-chromatographed on silica gel, with a 15:85 v:v mixture of ethyl acetate and hexane as eluent, to give N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide (19B), as an orange oil. was heated at reflux temperature for 4 hours extracted with ether The extract phase was washed with water dried (Na2SO4) filtered the solvent was evaporated from the filtrate The residue was flash-chromatographed on silica gel, with a 15:85 v v mixture of ethyl acetate and hexane as eluent

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

Procedure: A mixture of 9.0 g of 19A, 6.8 g of THPA and 100 mL of glacial acetic acid was heated at reflux temperature for 4 hours. The resulting mixture was cooled to room temperature, poured into 450 mL of water and extracted with ether. The extract phase was washed with water, dried (Na2SO4), and filtered, and the solvent was evaporated from the filtrate. The residue was flash-chromatographed on silica gel, with a 15:85 v:v mixture of ethyl acetate and hexane as eluent, to give N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide (19B), as an orange oil. was heated at reflux temperature for 4 hours extracted with ether The extract phase was washed with water dried (Na2SO4) filtered the solvent was evaporated from the filtrate The residue was flash-chromatographed on silica gel, with a 15:85 v v mixture of ethyl acetate and hexane as eluent

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

Procedure: A mixture of 4.4 g of THPA, 5.3 g of 3B and 60 mL of glacial acetic acid was refluxed for 1 hour, then poured into 300 mL of ice water. The resulting mixture was allowed to stand for 10 minutes, then filtered. The collected solid was washed with cold water, dried under reduced pressure and recrystallized from ethyl acetate/hexane, to give N-(3-(allyloxy)-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide (3C), as yellow crystals, m.p.: 118.5°-120° C. was refluxed for 1 hour filtered The collected solid was washed with cold water dried under reduced pressure recrystallized from ethyl acetate/hexane

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

Procedure: A mixture of 4.4 g of THPA, 5.3 g of 3B and 60 mL of glacial acetic acid was refluxed for 1 hour, then poured into 300 mL of ice water. The resulting mixture was allowed to stand for 10 minutes, then filtered. The collected solid was washed with cold water, dried under reduced pressure and recrystallized from ethyl acetate/hexane, to give N-(3-(allyloxy)-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide (3C), as yellow crystals, m.p.: 118.5°-120° C. was refluxed for 1 hour filtered The collected solid was washed with cold water dried under reduced pressure recrystallized from ethyl acetate/hexane

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

Procedure: 4-cyclohexene-1,2-dicarboxylic acid anhydride is dissolved in three times its quantity of dimethyl formamide. Its equimolar quantity of acetonitrile palladium dichloride is added at 40° C. in the course of 2 hours. Dimethyl formamide and acetonitrile are distilled off at 45° C./25 mbar. A brownish solid with a melting point of 53°-54° C. is obtained in a 90% yield. Isobutylvinyl ether palladium dichloride is obtained in analogous manner from acetonitrile palladium dichloride and isobutyl vinyl ether, melting point 57°-60° C. Dimethyl formamide and acetonitrile are distilled off at 45° C./25 mbar A brownish solid with a melting point of 53°-54° C. is obtained in a 90% yield