7-methoxy-1-benzofuran-2-carbaldehyde

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-Formyl-7-methoxybenzofuran (1.0 g) was stirred in dichloromethane (10 ml) under nitrogen at 0° C. Sodium acetate (1.4 g) was added followed by the dropwise addition of bromine (0.29 ml). Further dichloromethane (20 ml) was added to the mixture to facilitate stirring and the mixture was stirred overnight. The reaction mixture was diluted with dichloromethane (40 ml) and washed with water (30 ml). Drying over magnesium sulfate followed by removal of the solvent in vacuo gave a pale orange solid. Purification by flash chromatography on silica eluting with 10% ethyl acetate in hexane gave the title compound (0.50 g) as a beige solid. the mixture was stirred overnight washed with water (30 ml) Drying over magnesium sulfate followed by removal of the solvent in vacuo gave a pale orange solid Purification by flash chromatography on silica eluting with 10% ethyl acetate in hexane

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

Procedure: 2-Formyl-7-methoxybenzofuran (1.0 g) was stirred in dichloromethane (10 ml) under nitrogen at 0° C. Sodium acetate (1.4 g) was added followed by the dropwise addition of bromine (0.29 ml). Further dichloromethane (20 ml) was added to the mixture to facilitate stirring and the mixture was stirred overnight. The reaction mixture was diluted with dichloromethane (40 ml) and washed with water (30 ml). Drying over magnesium sulfate followed by removal of the solvent in vacuo gave a pale orange solid. Purification by flash chromatography on silica eluting with 10% ethyl acetate in hexane gave the title compound (0.50 g) as a beige solid. the mixture was stirred overnight washed with water (30 ml) Drying over magnesium sulfate followed by removal of the solvent in vacuo gave a pale orange solid Purification by flash chromatography on silica eluting with 10% ethyl acetate in hexane

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

Procedure: 2-(2-Formyl-6-methoxyphenoxy)acetaldehyde, dimethyl acetal (31 g) was heated to reflux in glacial acetic acid (120 ml) overnight. The mixture was then cooled and the solvent removed in vacuo to give a red oil. Purification by Kugelrohr distillation gave the title compound (17 g) as a pale yellow oil which solidified on standing. The mixture was then cooled the solvent removed in vacuo to give a red oil Purification by Kugelrohr distillation

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

Procedure: 2-Cyano-7-methoxybenzofuran (0.736 g) was dissolved in dichloromethane (10 ml), and a 1.02N DIBAL solution (5.4 ml) in toluene was added thereto at −4 to −30° C., followed by stirring for one hour. Methanol and dilute hydrochloric acid were added to the mixture, and the solvent was distilled off. The obtained residue was purified by column chromatography (hexane/ethyl acetate=10/1) to give Compound IIad-a (0.371 g, 50%) as an oily substance. at −4 to −30° C. the solvent was distilled off The obtained residue was purified by column chromatography (hexane/ethyl acetate=10/1) to give Compound IIad-a (0.371 g, 50%) as an oily substance

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

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of dried magnesium turnings (0.42 g) in anhydrous tetrahydrofuran (20 ml) was treated with 2 ml of (3-Bromopropoxy)-tert-butyldimethylsilane (4.4 g) in anhydrous tetrahydrofuran (10 ml) at room temperature under a dry nitrogen atmosphere. Initiation was achieved by the addition of catalytic iodine and warming to 80° C. The remaining solution (8 ml) was then added carefully. The reaction was cooled to −5° C. and a solution of 7-methoxybenzofuran-2-carbaldehyde (3 g) in anhydrous tetrahydrofuran (20 ml) was added carefully. After stirring at ambient temperature overnight the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous ammonium chloride solution (100 ml). The organic extract was dried over magnesium sulphate, filtered and preadsorbed onto silica. Purification by column chromatography on silica eluting with 10% ethyl acetate in hexane afforded the title compound as a yellow oil (4.88 g). The reaction was cooled to −5° C. was removed in vacuo The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous ammonium chloride solution (100 ml) The organic extract was dried over magnesium sulphate filtered Purification by column chromatography on silica eluting with 10% ethyl acetate in hexane

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of dried magnesium turnings (0.42 g) in anhydrous tetrahydrofuran (20 ml) was treated with 2 ml of (3-Bromopropoxy)-tert-butyldimethylsilane (4.4 g) in anhydrous tetrahydrofuran (10 ml) at room temperature under a dry nitrogen atmosphere. Initiation was achieved by the addition of catalytic iodine and warming to 80° C. The remaining solution (8 ml) was then added carefully. The reaction was cooled to −5° C. and a solution of 7-methoxybenzofuran-2-carbaldehyde (3 g) in anhydrous tetrahydrofuran (20 ml) was added carefully. After stirring at ambient temperature overnight the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous ammonium chloride solution (100 ml). The organic extract was dried over magnesium sulphate, filtered and preadsorbed onto silica. Purification by column chromatography on silica eluting with 10% ethyl acetate in hexane afforded the title compound as a yellow oil (4.88 g). The reaction was cooled to −5° C. was removed in vacuo The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous ammonium chloride solution (100 ml) The organic extract was dried over magnesium sulphate filtered Purification by column chromatography on silica eluting with 10% ethyl acetate in hexane

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of dried magnesium turnings (0.42 g) in anhydrous tetrahydrofuran (20 ml) was treated with 2 ml of (3-Bromopropoxy)-tert-butyldimethylsilane (4.4 g) in anhydrous tetrahydrofuran (10 ml) at room temperature under a dry nitrogen atmosphere. Initiation was achieved by the addition of catalytic iodine and warming to 80° C. The remaining solution (8 ml) was then added carefully. The reaction was cooled to −5° C. and a solution of 7-methoxybenzofuran-2-carbaldehyde (3 g) in anhydrous tetrahydrofuran (20 ml) was added carefully. After stirring at ambient temperature overnight the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous ammonium chloride solution (100 ml). The organic extract was dried over magnesium sulphate, filtered and preadsorbed onto silica. Purification by column chromatography on silica eluting with 10% ethyl acetate in hexane afforded the title compound as a yellow oil (4.88 g). The reaction was cooled to −5° C. was removed in vacuo The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous ammonium chloride solution (100 ml) The organic extract was dried over magnesium sulphate filtered Purification by column chromatography on silica eluting with 10% ethyl acetate in hexane

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

Procedure: Sodium borohydride (0.462 g) was added in one portion to a stirred solution of 7-methoxybenzofuran-2-carbaldehyde (2.15 g) in methanol (50 ml) at room temperature and the reaction was stirred for 3 hours. The reaction mixture was then diluted with water (100 ml) and extracted with dichloromethane (3×30 ml). The organic extracts were combined, washed with water (30 ml), dried over magnesium sulphate, filtered and the solvent removed in vacuo to afford the title compound (2.10 g) as a pale orange liquid. extracted with dichloromethane (3×30 ml) washed with water (30 ml) dried over magnesium sulphate filtered the solvent removed in vacuo