3-benzylidene-2-benzofuran-1-one

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

Procedure: To a solution of p-bromothioanisole (2.04 g, 10 mmol) in THF (40 mL) cooled to -78° C. was added a solution of n-butyl lithium in hexane (4.0 mL of 2.5M, 10 mmol). The resulting suspension was stirred at this temperature for 20 min. Then a solution of benzalphthalide (2.11 g, 9.5 mmol) in benzene (20 mL) was added and the reaction was allowed to proceed at r.t. for 2 hrs. The reaction turned deep-red. The reaction was completed by addition of conc. H2SO4 (0.63 mL, 20 mmol) and stirred at r.t. for another 30 min. The reaction was then diluted with EtOAc and a 1:1 mixture of H2O and saturated aqueous NaHCO3 and extracted. The aqueous layer was extracted one more time with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to dryness. The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane to give the title compound as an orange-red gum. to proceed at r.t. for 2 hrs stirred at r.t. for another 30 min extracted The aqueous layer was extracted one more time with EtOAc The combined organic extracts were dried over MgSO4 concentrated to dryness The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane

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

Procedure: To a solution of p-bromothioanisole (2.04 g, 10 mmol) in THF (40 mL) cooled to -78° C. was added a solution of n-butyl lithium in hexane (4.0 mL of 2.5M, 10 mmol). The resulting suspension was stirred at this temperature for 20 min. Then a solution of benzalphthalide (2.11 g, 9.5 mmol) in benzene (20 mL) was added and the reaction was allowed to proceed at r.t. for 2 hrs. The reaction turned deep-red. The reaction was completed by addition of conc. H2SO4 (0.63 mL, 20 mmol) and stirred at r.t. for another 30 min. The reaction was then diluted with EtOAc and a 1:1 mixture of H2O and saturated aqueous NaHCO3 and extracted. The aqueous layer was extracted one more time with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to dryness. The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane to give the title compound as an orange-red gum. to proceed at r.t. for 2 hrs stirred at r.t. for another 30 min extracted The aqueous layer was extracted one more time with EtOAc The combined organic extracts were dried over MgSO4 concentrated to dryness The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane

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

Procedure: To a solution of p-bromothioanisole (2.04 g, 10 mmol) in THF (40 mL) cooled to −78° C. was added a solution of n-butyl lithium in hexane (4.0 mL of 2.5 M, 10 mmol). The resulting suspension was stirred at this temperature for 20 min. Then a solution of benzalphthalide (2.11 g, 9.5 mmol) in benzene (20 mL) was added and the reaction was allowed to proceed at r.t. for 2 hrs. The reaction turned deep-red. The reaction was completed by addition of conc. H2SO4 (0.63 mL, 20 mmol) and stirred at r.t. for another 30 min. The reaction was then diluted with EtOAc and a 1:1 mixture of H2O and saturated aqueous NaHCO3 and extracted. The aqueous layer was extracted one more time with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to dryness. The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane to give the title compound as an orange-red gum. to proceed at r.t. for 2 hrs stirred at r.t. for another 30 min extracted The aqueous layer was extracted one more time with EtOAc The combined organic extracts were dried over MgSO4 concentrated to dryness The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane

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

Procedure: To a solution of p-bromothioanisole (2.04 g, 10 mmol) in THF (40 mL) cooled to −78° C. was added a solution of n-butyl lithium in hexane (4.0 mL of 2.5 M, 10 mmol). The resulting suspension was stirred at this temperature for 20 min. Then a solution of benzalphthalide (2.11 g, 9.5 mmol) in benzene (20 mL) was added and the reaction was allowed to proceed at r.t. for 2 hrs. The reaction turned deep-red. The reaction was completed by addition of conc. H2SO4 (0.63 mL, 20 mmol) and stirred at r.t. for another 30 min. The reaction was then diluted with EtOAc and a 1:1 mixture of H2O and saturated aqueous NaHCO3 and extracted. The aqueous layer was extracted one more time with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to dryness. The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane to give the title compound as an orange-red gum. to proceed at r.t. for 2 hrs stirred at r.t. for another 30 min extracted The aqueous layer was extracted one more time with EtOAc The combined organic extracts were dried over MgSO4 concentrated to dryness The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane

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

Procedure: To a solution of p-bromothioanisole (2.04 g, 10 mmol) in THF (40 mL) cooled to −78° C. was added a solution of n-butyl lithium in hexane (4.0 mL of 2.5 M, 10 mmol). The resulting suspension was stirred at this temperature for 20 min. Then a solution of benzalphthalide (2.11 g, 9.5 mmol) in benzene (20 mL) was added and the reaction was allowed to proceed at r.t. for 2 hrs. The reaction turned deep-red. The reaction was completed by addition of conc. H2SO4 (0.63 mL, 20 mmol) and stirred at r.t. for another 30 min. The reaction was then diluted with EtOAc and a 1:1 mixture of H2O and saturated aqueous NaHCO3 and extracted. The aqueous layer was extracted one more time with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to dryness. The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane to give the title compound as an orange-red gum. to proceed at r.t. for 2 hrs stirred at r.t. for another 30 min extracted The aqueous layer was extracted one more time with EtOAc The combined organic extracts were dried over MgSO4 concentrated to dryness The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane

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

Procedure: Diethyl methylphosphonate (1.94 g.) suspended in 50 ml. of dry tetrahydrofuran is treated with 1.1 equivalents of butyl lithium in hexane under nitrogen at about -78°. After 10 minutes, one equivalent of benzalphthalide in 10 ml. of tetrahydrofuran is added while maintaining the temperature at about -78°. The reaction mixture is allowed to warm to room temperature and then left to stand at room temperature for 3 hours. The reaction mixture is diluted with water and then extracted with ether. The ether extracts are combined, washed with water, dried and the solvent removed under vacuum. The residue is chromatographed on silica eluting with methylene chloride:hexane (4:1) to afford 3-benzylind-2-en-1-one and a small amount of starting material. while maintaining the temperature at about -78° left to stand at room temperature for 3 hours extracted with ether washed with water dried the solvent removed under vacuum The residue is chromatographed on silica eluting with methylene chloride:hexane (4:1)

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

Procedure: To a solution of p-bromothioanisole (2.04 g, 10 mmol) in THF (40 mL) cooled to -78° C. was added a solution of n-butyl lithium in hexane (4.0 mL of 2.5M, 10 mmol). The resulting suspension was stirred at this temperature for 20 min. Then a solution of benzalphthalide (2.11 g, 9.5 mmol) in benzene (20 mL) was added and the reaction was allowed to proceed at r.t. for 2 hrs. The reaction turned deep-red. The reaction was completed by addition of conc. H2SO4 (0.63 mL, 20 mmol) and stirred at r.t. for another 30 min. The reaction was then diluted with EtOAc and a 1:1 mixture of H2O and saturated aqueous NaHCO3 and extracted. The aqueous layer was extracted one more time with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated to dryness. The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane to give the title compound as an orange-red gum. to proceed at r.t. for 2 hrs stirred at r.t. for another 30 min extracted The aqueous layer was extracted one more time with EtOAc The combined organic extracts were dried over MgSO4 concentrated to dryness The crude product was purified by flash chromatography eluted with 10-15% EtOAc in hexane