dipropan-2-yl butanedioate

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 36 mL of t-amyl alcohol, 7.3 g of potassium-t-butoxide were solved, and then 10 g of 1-naphthonitrile were added stirring the solution at 90° C. Into the solution, 6.7 mL of diisopropyl succinate were dropped taking time for 2 hours and were placed under reflux for one day. Next, 30 mL of methanol and 4.4 mL of acetic acid were added at 60° C. and then refluxed for 30 minutes. After cooling, the product was separated out through a filter and subsequently rinsed with methanol, thus resulting in a red powder. Next, 2.89 g of the resulting red powder were dissolved in 80 mL of DMF, and 2.1 g of potassium-t-butoxide were added and stirred for one hour. Then, 1.5 mL of methyl iodide was added and stirred at 65° C. for one day. After 50 mL of water was added, extraction was performed with dichloromethane. The extract was concentrated and refined through a column chromatography with silica gel and thus results in 1.5 g of yellow powder. The following is the results of 1H-NMR analysis. for 2 hours under reflux for one day refluxed for 30 minutes After cooling the product was separated out through a filter subsequently rinsed with methanol thus resulting in a red powder stirred for one hour stirred at 65° C. for one day extraction The extract was concentrated

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium metal (6.90 g, 0.30 mol) was added to 100 ml t-amyl alcohol and a small amount of iron (III) chloride (100 mg) was added. The mixture was stirred vigorously for 2 hr at 105° C. until the sodium dissolved. The solution was cooled to 85° C. and 2-thiophenecarbonitrile (22.0 g, 0.2 mol) was added. Diisopropyl succinate (16.6 g, 0.08 mol) dissolved in 10 ml of t-amyl alcohol was added dropwise to the reaction mixture over 1 hr at 85° C. The reaction mixture was stirred at this temperature for 12 hrs, then cooled to 50° C., diluted with 100 ml of methanol, and then slowly neutralized with 30 ml of glacial acetic acid and refluxed briefly, and then filtered. The residue was washed several times with hot methanol and water, and the resultant solid was dried in a vacuum oven at 50° C. A dark red color powder was obtained which was used without further purification (20 g, 83%). dissolved was added dropwise to the reaction mixture over 1 hr at 85° C cooled to 50° C. refluxed briefly filtered The residue was washed several times with hot methanol and water the resultant solid was dried in a vacuum oven at 50° C A dark red color powder was obtained which was used without further purification (20 g, 83%)

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium metal (6.90 g, 0.30 mol) was added to 100 ml t-amyl alcohol and a small amount of iron (III) chloride (100 mg) was added. The mixture was stirred vigorously for 2 hr at 105° C. until the sodium dissolved. The solution was cooled to 85° C. and 2-thiophenecarbonitrile (22.0 g, 0.2 mol) was added. Diisopropyl succinate (16.6 g, 0.08 mol) dissolved in 10 ml of t-amyl alcohol was added dropwise to the reaction mixture over 1 hr at 85° C. The reaction mixture was stirred at this temperature for 12 hrs, then cooled to 50° C., diluted with 100 ml of methanol, and then slowly neutralized with 30 ml of glacial acetic acid and refluxed briefly, and then filtered. The residue was washed several times with hot methanol and water, and the resultant solid was dried in a vacuum oven at 50° C. A dark red color powder was obtained which was used without further purification (20 g, 83%). dissolved was added dropwise to the reaction mixture over 1 hr at 85° C cooled to 50° C. refluxed briefly filtered The residue was washed several times with hot methanol and water the resultant solid was dried in a vacuum oven at 50° C A dark red color powder was obtained which was used without further purification (20 g, 83%)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 36 mL of t-amyl alcohol, 7.3 g of potassium-t-butoxide were solved, and then 10 g of 1-naphthonitrile were added stirring the solution at 90° C. Into the solution, 6.7 mL of diisopropyl succinate were dropped taking time for 2 hours and were placed under reflux for one day. Next, 30 mL of methanol and 4.4 mL of acetic acid were added at 60° C. and then refluxed for 30 minutes. After cooling, the product was separated out through a filter and subsequently rinsed with methanol, thus resulting in a red powder. Next, 2.89 g of the resulting red powder were dissolved in 80 mL of DMF, and 2.1 g of potassium-t-butoxide were added and stirred for one hour. Then, 1.5 mL of methyl iodide was added and stirred at 65° C. for one day. After 50 mL of water was added, extraction was performed with dichloromethane. The extract was concentrated and refined through a column chromatography with silica gel and thus results in 1.5 g of yellow powder. The following is the results of 1H-NMR analysis. for 2 hours under reflux for one day refluxed for 30 minutes After cooling the product was separated out through a filter subsequently rinsed with methanol thus resulting in a red powder stirred for one hour stirred at 65° C. for one day extraction The extract was concentrated

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 36 mL of t-amyl alcohol, 7.3 g of potassium-t-butoxide were solved, and then 10 g of 1-naphthonitrile were added stirring the solution at 90° C. Into the solution, 6.7 mL of diisopropyl succinate were dropped taking time for 2 hours and were placed under reflux for one day. Next, 30 mL of methanol and 4.4 mL of acetic acid were added at 60° C. and then refluxed for 30 minutes. After cooling, the product was separated out through a filter and subsequently rinsed with methanol, thus resulting in a red powder. Next, 2.89 g of the resulting red powder were dissolved in 80 mL of DMF, and 2.1 g of potassium-t-butoxide were added and stirred for one hour. Then, 1.5 mL of methyl iodide was added and stirred at 65° C. for one day. After 50 mL of water was added, extraction was performed with dichloromethane. The extract was concentrated and refined through a column chromatography with silica gel and thus results in 1.5 g of yellow powder. The following is the results of 1H-NMR analysis. for 2 hours under reflux for one day refluxed for 30 minutes After cooling the product was separated out through a filter subsequently rinsed with methanol thus resulting in a red powder stirred for one hour stirred at 65° C. for one day extraction The extract was concentrated

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium metal (6.90 g, 0.30 mol) was added to 100 ml t-amyl alcohol and a small amount of iron (III) chloride (100 mg) was added. The mixture was stirred vigorously for 2 hr at 105° C. until the sodium dissolved. The solution was cooled to 85° C. and 2-thiophenecarbonitrile (22.0 g, 0.2 mol) was added. Diisopropyl succinate (16.6 g, 0.08 mol) dissolved in 10 ml of t-amyl alcohol was added dropwise to the reaction mixture over 1 hr at 85° C. The reaction mixture was stirred at this temperature for 12 hrs, then cooled to 50° C., diluted with 100 ml of methanol, and then slowly neutralized with 30 ml of glacial acetic acid and refluxed briefly, and then filtered. The residue was washed several times with hot methanol and water, and the resultant solid was dried in a vacuum oven at 50° C. A dark red color powder was obtained which was used without further purification (20 g, 83%). dissolved was added dropwise to the reaction mixture over 1 hr at 85° C cooled to 50° C. refluxed briefly filtered The residue was washed several times with hot methanol and water the resultant solid was dried in a vacuum oven at 50° C A dark red color powder was obtained which was used without further purification (20 g, 83%)

Conditions: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: As a specific example embodiment, potassium tert-butoxide (67.4 g, 0.60 mol) and tert-amyl alcohol (400 mL) are added to a nitrogen-protected oven-dried three-neck round-bottom flask equipped with a mechanical stirrer, a thermometer and a reflux condenser. The mixture is heated to 105° C. for 1.5 h and to this mixture is added 2-thiophenenitrile (55.2 g, 0.50 mol) and the stirring continued at 105° C. for 30 min. A mixture of diisopropyl succinate (40.4 g, 0.20 mol) in tert-amyl alcohol (60 mL) is added dropwise over a period of 3 h with rapid stirring. The mixture is then stirred at 105° C. for a further 2 h, then cooled to 50° C., at which point a mixture of methanol (300 mL) and water (80 mL) is added. The reaction mixture is heated at reflux for 45 min before cooling to room temperature. The mixture is poured over 500 g of ice, then concentrated hydrochloric acid (35% aq) (150 mL) and methanol (750 mL) are added and the mixture is stirred for 45 min. The mixture is filtered and the solid is washed with methanol (200 mL). The solid is then suspended in water (1 L) and stirred for 30 min before being filtered again. This suspension in water, stirring and filtration is repeated a further three times. After filtering for the last time, the solid is oven dried at 80° C. for 16 h, then dried under vacuum to give the product, 3,6-bis(thiophen-2-yl)-2H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione, (49.7 g, 82% yield) as a red solid. This compound is used without further purification. 1HNMR (d6-DMSO, 300 MHz): δ 7.27 (2H, t, J=3.0), 7.89 (2H, dd, J1=6.0, J2=3.0), 8.23 (2H, d, J=3.0), 11.00 (2H, s); 13CNMR (d6-DMSO, 75 MHz): δ 113.6 (2C), 127.1 (2C), 128.3 (2C), 130.5 (2C), 136.6 (2C), 142.6 (2C), 168.2 (2C); m/z (EI+) 300.0 [M]+; Anal. Calc. for C14H8N2O2S2: C, 55.98; H, 2.68; N, 9.33; S, 21.35. equipped with a mechanical stirrer is added dropwise over a period of 3 h with rapid stirring cooled to 50° C., at which point is added The reaction mixture is heated at reflux for 45 min before cooling to room temperature the mixture is stirred for 45 min The mixture is filtered the solid is washed with methanol (200 mL) stirred for 30 min before being filtered again This suspension in water, stirring filtration After filtering for the last time dried at 80° C. for 16 h dried under vacuum

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Fine pieces of sodium metal (6.90 g, 0.30 mol) were added to 100 mL t-amyl alcohol and a small amount of iron (iii) chloride (100 mg) was added. The mixture was stirred vigorously for 2 hr at 105° C. until sodium disappeared. The solution was cooled at 85° C. 2-Thiophenecarbonitrile (22.0 g, 0.2 mol) was added to the resultant solution. Then diisopropyl succinate (16.6 g, 0.08 mol) was dissolved in 10 mL of t-amyl alcohol and added drop wise over 1 hr at 85° C. Reaction was stirred at this temperature for 12 hrs. The reaction mixture was then cooled to 50° C., diluted with 100 mL of methanol, and then slowly neutralized with 30 ml of glacial acetic acid and refluxed briefly, and the reaction mixture was filtered. After the residue was washed several times with hot methanol and water, the resultant solid was dried in vacuum oven at 50° C. A dark red colored powder was obtained which was used further without purification (20 g, 83%). added drop wise over 1 hr at 85° C Reaction The reaction mixture was then cooled to 50° C. refluxed briefly the reaction mixture was filtered After the residue was washed several times with hot methanol and water the resultant solid was dried in vacuum oven at 50° C A dark red colored powder was obtained which was used further without purification (20 g, 83%)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 36 mL of t-amyl alcohol, 7.3 g of potassium-t-butoxide were solved, and then 10 g of 1-naphthonitrile were added stirring the solution at 90° C. Into the solution, 6.7 mL of diisopropyl succinate were dropped taking time for 2 hours and were placed under reflux for one day. Next, 30 mL of methanol and 4.4 mL of acetic acid were added at 60° C. and then refluxed for 30 minutes. After cooling, the product was separated out through a filter and subsequently rinsed with methanol, thus resulting in a red powder. Next, 2.89 g of the resulting red powder were dissolved in 80 mL of DMF, and 2.1 g of potassium-t-butoxide were added and stirred for one hour. Then, 1.5 mL of methyl iodide was added and stirred at 65° C. for one day. After 50 mL of water was added, extraction was performed with dichloromethane. The extract was concentrated and refined through a column chromatography with silica gel and thus results in 1.5 g of yellow powder. The following is the results of 1H-NMR analysis. for 2 hours under reflux for one day refluxed for 30 minutes After cooling the product was separated out through a filter subsequently rinsed with methanol thus resulting in a red powder stirred for one hour stirred at 65° C. for one day extraction The extract was concentrated