methyl 2-(1-benzofuran-2-yl)acetate

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

Procedure: A solution of 2-coumaranone (5.0 g, 37 mmol) and methyl(triphenylphosphoranylideneacetate) (13.5 g. 40 mmol) in toluene (70 mL) was heated to reflux for 25 hours. More toluene was added (10 mL), and after a further 5 hours, more methyl(triphenylphosphoranylideneacetate) (0.5 g, 1.5 mmol). After another 19 hours, a further 1.0 g (3.0 mmol) was added, and after a further 21 hours, the solvent was removed in vacuo. Column chromatography (heptane:ethyl acetate 4:1) gave the product as a brown oil, 28 mmol, 75%. to reflux for 25 hours After another 19 hours a further 1.0 g (3.0 mmol) was added after a further 21 hours the solvent was removed in vacuo

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

Procedure: Benzofarane-2-acetic acid 4 (305 g, 1.73 mol) was dissolved in methanol (1,000 ml) and concentrated sulfuric acid (20 ml). The mixture, which was originally a suspension, was stirred at reflux for 120 minutes. Half of the methanol was distilled off and a mixture consisting of water, KOH, and ethyl acetate (2,000 ml/65 g/1,000 ml) was added. After mixing well, the organic layer was allowed to separate and was isolated. The aqueous phase was extracted once more with ethyl acetate (500 ml) and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The crude product was a reddish oil weighing 316 g, which was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.). The yield of distilled product, a colorless oil, was 288 g (1.51 mol, 86%). Anal. (C11H10O3) C, H: calculated 69.46, 5.30; found 69.49, 5.36. at reflux for 120 minutes Half of the methanol was distilled off was added After mixing well to separate was isolated The aqueous phase was extracted once more with ethyl acetate (500 ml) the combined organic extracts were dried over sodium sulfate filtered evaporated was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.)

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

Procedure: Benzofarane-2-acetic acid 4 (305 g, 1.73 mol) was dissolved in methanol (1,000 ml) and concentrated sulfuric acid (20 ml). The mixture, which was originally a suspension, was stirred at reflux for 120 minutes. Half of the methanol was distilled off and a mixture consisting of water, KOH, and ethyl acetate (2,000 ml/65 g/1,000 ml) was added. After mixing well, the organic layer was allowed to separate and was isolated. The aqueous phase was extracted once more with ethyl acetate (500 ml) and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The crude product was a reddish oil weighing 316 g, which was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.). The yield of distilled product, a colorless oil, was 288 g (1.51 mol, 86%). Anal. (C11H10O3) C, H: calculated 69.46, 5.30; found 69.49, 5.36. at reflux for 120 minutes Half of the methanol was distilled off was added After mixing well to separate was isolated The aqueous phase was extracted once more with ethyl acetate (500 ml) the combined organic extracts were dried over sodium sulfate filtered evaporated was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.)

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

Procedure: A solution of Example 8 (5.32 g, 28 mmol) and lithium hydroxide monohydrate (1.24 g, 30 mmol) in tetrahydrofuran (45 mL), water (30 mL), and methanol (12 mL) was stirred for 5 hours at room temperature. Water (60 mL) was added, and the reaction mixture was acidified to pH 4 using 2 M HCl and extracted with dichloromethane (5×150 mL). The organics were dried (MgSO4) and the solvent removed in vacuo. Column chromatography (ethyl acetate:heptane 4:1→ethyl acetate:methanol) gave a brown solid. This was dissolved in ethyl acetate, heptane was added, and the mixture was stirred overnight. Solvent was removed by syringe to give product as a pale brown solid, 17 mmol, 61%. extracted with dichloromethane (5×150 mL) The organics were dried (MgSO4) the solvent removed in vacuo Column chromatography (ethyl acetate:heptane 4:1→ethyl acetate:methanol) gave a brown solid Solvent was removed by syringe to give product as a pale brown solid, 17 mmol, 61%

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

Procedure: A solution of 2-coumaranone (5.0 g, 37 mmol) and methyl(triphenylphosphoranylideneacetate) (13.5 g, 40 mmol) in toluene (70 mL) was heated to reflux for 25 hours. More toluene was added (10 mL), and after a further 5 hours, more methyl(triphenylphosphoranylideneacetate) (0.5 g, 1.5 mmol). After another 19 hours, a further 1.0 g (3.0 mmol) was added, and after a further 21 hours, the solvent was removed in vacuo. Column chromatography (heptane:ethyl acetate 4:1) gave the product as a brown oil, 28 mmol, 75%. to reflux for 25 hours After another 19 hours a further 1.0 g (3.0 mmol) was added after a further 21 hours the solvent was removed in vacuo

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

Procedure: A solution of 2-coumaranone (5.0 g, 37 mmol) and methyl(triphenylphosphoranylideneacetate) (13.5 g, 40 mmol) in toluene (70 mL) was heated to reflux for 25 hours. More toluene was added (10 mL), and after a further 5 hours, more methyl(triphenylphosphoranylideneacetate) (0.5 g, 1.5 mmol). After another 19 hours, a further 1.0 g (3.0 mmol) was added, and after a further 21 hours, the solvent was removed in vacuo. Column chromatography (heptane:ethyl acetate 4:1) gave the product as a brown oil, 28 mmol, 75%. to reflux for 25 hours After another 19 hours a further 1.0 g (3.0 mmol) was added after a further 21 hours the solvent was removed in vacuo

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

Procedure: Benzofurane-2-acetic acid 4 (305 g, 1.73 mol) was dissolved in methanol (1,000 ml) and concentrated sulfuric acid (20 ml). The mixture, which was originally a suspension, was stirred at reflux for 120 minutes. Half of the methanol was distilled off and a mixture consisting of water, KOH, and ethyl acetate (2,000 ml/65 g/1,000 ml) was added. After mixing well, the organic layer was allowed to separate and was isolated. The aqueous phase was extracted once more with ethyl acetate (500 ml) and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The crude product was a reddish oil weighing 316 g, which was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.). The yield of distilled product, a colorless oil, was 288 g (1.51 mol, 86%). Anal. (C11H10O3) C, H: calculated 69.46, 5.30; found 69.49, 5.36. at reflux for 120 minutes Half of the methanol was distilled off was added After mixing well to separate was isolated The aqueous phase was extracted once more with ethyl acetate (500 ml) the combined organic extracts were dried over sodium sulfate filtered evaporated was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.)

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

Procedure: A solution of 2-coumaranone (5.0 g, 37 mmol) and methyl(triphenylphosphoranylideneacetate) (13.5 g. 40 mmol) in toluene (70 mL) was heated to reflux for 25 hours. More toluene was added (10 mL), and after a further 5 hours, more methyl(triphenylphosphoranylideneacetate) (0.5 g, 1.5 mmol). After another 19 hours, a further 1.0 g (3.0 mmol) was added, and after a further 21 hours, the solvent was removed in vacuo. Column chromatography (heptane:ethyl acetate 4:1) gave the product as a brown oil, 28 mmol, 75%. to reflux for 25 hours After another 19 hours a further 1.0 g (3.0 mmol) was added after a further 21 hours the solvent was removed in vacuo

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

Procedure: A solution of 2-coumaranone (5.0 g, 37 mmol) and methyl(triphenylphosphoranylideneacetate) (13.5 g. 40 mmol) in toluene (70 mL) was heated to reflux for 25 hours. More toluene was added (10 mL), and after a further 5 hours, more methyl(triphenylphosphoranylideneacetate) (0.5 g, 1.5 mmol). After another 19 hours, a further 1.0 g (3.0 mmol) was added, and after a further 21 hours, the solvent was removed in vacuo. Column chromatography (heptane:ethyl acetate 4:1) gave the product as a brown oil, 28 mmol, 75%. to reflux for 25 hours After another 19 hours a further 1.0 g (3.0 mmol) was added after a further 21 hours the solvent was removed in vacuo

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

Procedure: Benzofarane-2-acetic acid 4 (305 g, 1.73 mol) was dissolved in methanol (1,000 ml) and concentrated sulfuric acid (20 ml). The mixture, which was originally a suspension, was stirred at reflux for 120 minutes. Half of the methanol was distilled off and a mixture consisting of water, KOH, and ethyl acetate (2,000 ml/65 g/1,000 ml) was added. After mixing well, the organic layer was allowed to separate and was isolated. The aqueous phase was extracted once more with ethyl acetate (500 ml) and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The crude product was a reddish oil weighing 316 g, which was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.). The yield of distilled product, a colorless oil, was 288 g (1.51 mol, 86%). Anal. (C11H10O3) C, H: calculated 69.46, 5.30; found 69.49, 5.36. at reflux for 120 minutes Half of the methanol was distilled off was added After mixing well to separate was isolated The aqueous phase was extracted once more with ethyl acetate (500 ml) the combined organic extracts were dried over sodium sulfate filtered evaporated was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.)

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

Procedure: Benzofurane-2-acetic acid 4 (305 g, 1.73 mol) was dissolved in methanol (1,000 ml) and concentrated sulfuric acid (20 ml). The mixture, which was originally a suspension, was stirred at reflux for 120 minutes. Half of the methanol was distilled off and a mixture consisting of water, KOH, and ethyl acetate (2,000 ml/65 g/1,000 ml) was added. After mixing well, the organic layer was allowed to separate and was isolated. The aqueous phase was extracted once more with ethyl acetate (500 ml) and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The crude product was a reddish oil weighing 316 g, which was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.). The yield of distilled product, a colorless oil, was 288 g (1.51 mol, 86%). Anal. (C11H10O3) C, H: calculated 69.46, 5.30; found 69.49, 5.36. at reflux for 120 minutes Half of the methanol was distilled off was added After mixing well to separate was isolated The aqueous phase was extracted once more with ethyl acetate (500 ml) the combined organic extracts were dried over sodium sulfate filtered evaporated was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.)

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

Procedure: Benzofurane-2-acetic acid 4 (305 g, 1.73 mol) was dissolved in methanol (1,000 ml) and concentrated sulfuric acid (20 ml). The mixture, which was originally a suspension, was stirred at reflux for 120 minutes. Half of the methanol was distilled off and a mixture consisting of water, KOH, and ethyl acetate (2,000 ml/65 g/1,000 ml) was added. After mixing well, the organic layer was allowed to separate and was isolated. The aqueous phase was extracted once more with ethyl acetate (500 ml) and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The crude product was a reddish oil weighing 316 g, which was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.). The yield of distilled product, a colorless oil, was 288 g (1.51 mol, 86%). Anal. (C11H10O3) C, H: calculated 69.46, 5.30; found 69.49, 5.36. at reflux for 120 minutes Half of the methanol was distilled off was added After mixing well to separate was isolated The aqueous phase was extracted once more with ethyl acetate (500 ml) the combined organic extracts were dried over sodium sulfate filtered evaporated was purified by flash vacuum distillation at 0.1 mm Hg (bp 80-90° C.)