[4-(2-hydroxyethyl)phenyl] methanesulfonate

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

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

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-Hexyloxy-3-(4-hydroxyphenyl)propanoic acid methyl ester (0.33 g, 1.19 mmole) and 2-(4-methanesulfonyloxyphenyl)ethanol (0.2578 g; 1.19 mmole) was dissolved in dichloromethane (5 ml) under argon. Azodicarbonyl dipiperidine (0.451 g; 1.789 mmole) was added followed by addition of triphenylphosphine (0.375 g; 1.423 mmole). The reaction mixture was stirred at room temperature and after 2 hours more dichloromethane (2 ml) was added. The reaction mixture was stirred for another 18 hours and then filtered. The filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine, dried with sodium sulfate and evaporated. Chromatography of the residue on silica gel using heptane:ethyl acetat (2:1 to 1:1) as eluant gave 0.381 g (67% yield) of 2-hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl ester. was added filtered The filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine dried with sodium sulfate evaporated

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

Procedure: 2-Hexyloxy-3-(4-hydroxyphenyl)propanoic acid methyl ester (0.33 g, 1.19 mmole) and 2-(4-methanesulfonyloxyphenyl)ethanol (0.2578 g; 1.19 mmole) was dissolved in dichloromethane (5 ml) under argon. Azodicarbonyl dipiperidine (0.451 g; 1.789 mmole) was added followed by addition of triphenylphosphine (0.375 g; 1.423 mmole). The reaction mixture was stirred at room temperature and after 2 hours more dichloromethane (2 ml) was added. The reaction mixture was stirred for another 18 hours and then filtered. The filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine, dried with sodium sulfate and evaporated. Chromatography of the residue on silica gel using heptane:ethyl acetat (2:1 to 1:1) as eluant gave 0.381 g (67% yield) of 2-hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl ester. was added filtered The filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine dried with sodium sulfate evaporated

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

Procedure: 0.28 g (0.623 mmole) 3-triphenylmethyl-5-([4-hydroxyphenyl]methyl)oxazolidine-2,4-dione was under argon atmosphere added to a cooled solution of 0.148 g (0.685 mmole) 2-[4-(methylsulfonyloxy)phenyl]-1-ethanol, 0.173 g (0.685 mmole) 1,1′-(azodicarbonyl)-dipiperidine and 0.18 g (0.685 mmole) triphenylphosphine in 6 ml dichloromethane. After stirring for 3 hours the reaction mixture was filtered and the crude product was purified by chromatography on silica gel using heptane:ethyl acetate (2:2) as eluent to give 0.215 g (yield 53%) of 3-triphenylmethyl-5-([4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl]methyl)oxazolidine-2,4-dione. was filtered the crude product was purified by chromatography on silica gel

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

Procedure: 2-Hexyloxy-3-(4-hydroxyphenyl)propanoic acid methyl ester (0.33 g, 1.19 mmole) and 2-(4-methanesulfonyloxyphenyl)ethanol (0.2578 g; 1.19 mmole) was dissolved in dichloromethane (5 ml) under argon. Azodicarbonyl dipiperidine (0.451 g; 1.789 mmole) was added followed by addition of triphenylphosphine (0.375 g; 1.423 mmole). The reaction mixture was stirred at room temperature and after 2 hours more dichloromethane (2 ml) was added. The reaction mixture was stirred for another 18 hours and then filtered. The filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine, dried with sodium sulfate and evaporated. Chromatography of the residue on silica gel using heptane:ethyl acetat (2:1 to 1:1) as eluant gave 0.381 g (67% yield) of 2-hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl ester. was added filtered The filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine dried with sodium sulfate evaporated