methyl 2-(3-sulfanylphenyl)acetate

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 2-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-2-ol (0.1 g, 0.351 mmol), (3-Mercapto-phenyl)-acetic acid methyl ester (0.070 g, 0.386 mmol), zinc (I) iodide (0.056 g, 0.176 mmol), and 1,2-dichloroethane (2 mL) is stirred at room temperature 24 hr. The reaction mixture is diluted with ethyl acetate (25 mL), and washed with aqueous saturated sodium hydrogen carbonate, water, brine (25 mL each), dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 8:2 hexanes:ethyl acetate to afford the product as a colorless film, 0.105 g, 66%. MS M++1 286. The structure is confirmed by 1H NMR spectroscopy. washed with aqueous saturated sodium hydrogen carbonate, water, brine (25 mL each) dried over anhydrous magnesium sulfate filtered concentrated purified via silica chromatography eluting with 8:2 hexanes ethyl acetate to afford the product as a colorless film, 0.105 g, 66%

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

Procedure: A mixture of (3-dimethylcarbamoylsulfanyl-phenyl)-acetic acid methyl ester (2.0 g, 7.9 mmol), potassium hydroxide (1.4 g, 24 mmol) methanol (50 mL), and water (5 mL) is stirred at reflux 3 hr. The mixture is concentrated, and product partitioned between 1M aqueous hydrochloric acid (50 mL) and ethyl acetate (3×75 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is taken up in methanol (50 mL), 2 mL concentrated sulfuric acid is added, and the mixture refluxed 3 hr. The mixture is concentrated, and the residue purified by silica chromatography eluting with 7:3 hexanes:ethyl acetate to afford the title compound as a pale yellow oil, 1.0 g, 69%. MS M++1 183. The structure is confirmed by 1H NMR spectroscopy. at reflux 3 hr The mixture is concentrated product partitioned between 1M aqueous hydrochloric acid (50 mL) and ethyl acetate (3×75 mL) The combined extracts are dried over anhydrous magnesium sulfate filtered concentrated 2 mL concentrated sulfuric acid is added the mixture refluxed 3 hr The mixture is concentrated the residue purified by silica chromatography eluting with 7:3 hexanes

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

Procedure: A mixture of (3-dimethylcarbamoylsulfanyl-phenyl)-acetic acid methyl ester (2.0 g, 7.9 mmol), potassium hydroxide (1.4 g, 24 mmol) methanol (50 mL), and water (5 mL) is stirred at reflux 3 hr. The mixture is concentrated, and product partitioned between 1M aqueous hydrochloric acid (50 mL) and ethyl acetate (3×75 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is taken up in methanol (50 mL), 2 mL concentrated sulfuric acid is added, and the mixture refluxed 3 hr. The mixture is concentrated, and the residue purified by silica chromatography eluting with 7:3 hexanes:ethyl acetate to afford the title compound as a pale yellow oil, 1.0 g, 69%. MS M++1 183. The structure is confirmed by 1H NMR spectroscopy. at reflux 3 hr The mixture is concentrated product partitioned between 1M aqueous hydrochloric acid (50 mL) and ethyl acetate (3×75 mL) The combined extracts are dried over anhydrous magnesium sulfate filtered concentrated 2 mL concentrated sulfuric acid is added the mixture refluxed 3 hr The mixture is concentrated the residue purified by silica chromatography eluting with 7:3 hexanes

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

Procedure: A mixture of (3-dimethylcarbamoylsulfanyl-phenyl)-acetic acid methyl ester (2.0 g, 7.9 mmol), potassium hydroxide (1.4 g, 24 mmol) methanol (50 mL), and water (5 mL) is stirred at reflux 3 hr. The mixture is concentrated, and product partitioned between 1M aqueous hydrochloric acid (50 mL) and ethyl acetate (3×75 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is taken up in methanol (50 mL), 2 mL concentrated sulfuric acid is added, and the mixture refluxed 3 hr. The mixture is concentrated, and the residue purified by silica chromatography eluting with 7:3 hexanes:ethyl acetate to afford the title compound as a pale yellow oil, 1.0 g, 69%. MS M++1 183. The structure is confirmed by 1H NMR spectroscopy. at reflux 3 hr The mixture is concentrated product partitioned between 1M aqueous hydrochloric acid (50 mL) and ethyl acetate (3×75 mL) The combined extracts are dried over anhydrous magnesium sulfate filtered concentrated 2 mL concentrated sulfuric acid is added the mixture refluxed 3 hr The mixture is concentrated the residue purified by silica chromatography eluting with 7:3 hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2-(3-mercaptophenyl)acetate (0.55 g, 3.0 mmol) was dissolved in 10 mL acetonitrile and potassium nitrate (0.76 g, 7.5 mmol) was added and the reaction mixture cooled to 0° C. To this suspension sulfuryl chloride was added (0.6 mL, 7.5 mmol) at 0° C. and the reaction mixture was let warm to room temperature and stirred overnight. A solution of saturated sodium bicarbonate was added followed by ethyl acetate (100 mL each). The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford methyl 2-(3-chlorosulfonylphenyl)acetate as an oil (0.59 g, 2.4 mmol, 79% yield). 1H NMR (CDCl3) 7.91 ppm, 2H, m; 7.60 ppm, 1H, d; 7.53 ppm, 1H, t; 3.73 ppm, 2H, s; 3.72 ppm, 3H, s. the reaction mixture was let warm to room temperature The organic layer was washed with brine dried over sodium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2-(3-mercaptophenyl)acetate (0.55 g, 3.0 mmol) was dissolved in 10 mL acetonitrile and potassium nitrate (0.76 g, 7.5 mmol) was added and the reaction mixture cooled to 0° C. To this suspension sulfuryl chloride was added (0.6 mL, 7.5 mmol) at 0° C. and the reaction mixture was let warm to room temperature and stirred overnight. A solution of saturated sodium bicarbonate was added followed by ethyl acetate (100 mL each). The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford methyl 2-(3-chlorosulfonylphenyl)acetate as an oil (0.59 g, 2.4 mmol, 79% yield). 1H NMR (CDCl3) 7.91 ppm, 2H, m; 7.60 ppm, 1H, d; 7.53 ppm, 1H, t; 3.73 ppm, 2H, s; 3.72 ppm, 3H, s. the reaction mixture was let warm to room temperature The organic layer was washed with brine dried over sodium sulfate concentrated

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

Procedure: 2-(3-Mercaptophenyl)acetic acid (1.0 g, 6.0 mmol) was dissolved in dry methanol (40 mL). To this solution 10 drops concentrated sulfuric acid was added and the reaction mixture was heated to reflux for 36 hours. The reaction mixture was then concentrated to about half the volume, diluted with ethyl acetate, and the organic layer washed with saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated to afford methyl 2-(3-mercaptophenyl)acetate as an oil (0.55 g, 3.0 mmol, 50% yield). 1H NMR (CDCl3) 7.05 ppm, 3H, m; 6.88 ppm, 1H, m; 3.53 ppm, 3H, s; 3.38 ppm, 2H, s. the reaction mixture was heated to reflux for 36 hours The reaction mixture was then concentrated to about half the volume diluted with ethyl acetate the organic layer washed with saturated sodium bicarbonate solution The organic layer was dried over sodium sulfate concentrated

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

Procedure: 2-(3-Mercaptophenyl)acetic acid (1.0 g, 6.0 mmol) was dissolved in dry methanol (40 mL). To this solution 10 drops concentrated sulfuric acid was added and the reaction mixture was heated to reflux for 36 hours. The reaction mixture was then concentrated to about half the volume, diluted with ethyl acetate, and the organic layer washed with saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated to afford methyl 2-(3-mercaptophenyl)acetate as an oil (0.55 g, 3.0 mmol, 50% yield). 1H NMR (CDCl3) 7.05 ppm, 3H, m; 6.88 ppm, 1H, m; 3.53 ppm, 3H, s; 3.38 ppm, 2H, s. the reaction mixture was heated to reflux for 36 hours The reaction mixture was then concentrated to about half the volume diluted with ethyl acetate the organic layer washed with saturated sodium bicarbonate solution The organic layer was dried over sodium sulfate concentrated

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2-(3-mercaptophenyl)acetate (0.55 g, 3.0 mmol) was dissolved in 10 mL acetonitrile and potassium nitrate (0.76 g, 7.5 mmol) was added and the reaction mixture cooled to 0° C. To this suspension sulfuryl chloride was added (0.6 mL, 7.5 mmol) at 0° C. and the reaction mixture was let warm to room temperature and stirred overnight. A solution of saturated sodium bicarbonate was added followed by ethyl acetate (100 mL each). The organic layer was washed with brine, dried over sodium sulfate and concentrated to an oil 0.59 g, 2.4 mmol, 79% yield. 1H NMR 500 MHz (CDCl3) 7.91 ppm, 2H, m; 7.60 ppm, 1H, d; 7.53 ppm, 1H, t; 3.73 ppm, 2H, s; 3.72 ppm, 3H, s. the reaction mixture was let warm to room temperature The organic layer was washed with brine dried over sodium sulfate