ethyl (2S)-2-hydroxy-3-phenylpropanoate

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

Procedure: To a solution of 4-[1-(4-heptyloxyphenyl)-5-methyl-1H-pyrrol-2-yl]phenol (640 mg, 1.76 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (513 mg, 2.64 mmol) and triphenylphosphine (692 mg, 2.64 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (666 mg, 2.64 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 240 mg (yield: 25.2%) the mixture was extracted with ethyl acetate The extract was dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: To a solution of 4-[5-methyl-1-(4-octyloxyphenyl)-1H-pyrrol-2-yl]phenol (740 mg, 1.96 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (570 mg, 2.94 mmol) and triphenylphosphine (770 mg, 2.94 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (741 mg, 2.94 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 420 mg (yield: 39.6%) the mixture was extracted with ethyl acetate The extract was dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: To a solution of 4-[5-methyl-1-(4-octyloxyphenyl)-1H-pyrrol-2-yl]phenol (740 mg, 1.96 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (570 mg, 2.94 mmol) and triphenylphosphine (770 mg, 2.94 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (741 mg, 2.94 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 420 mg (yield: 39.6%) the mixture was extracted with ethyl acetate The extract was dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: To a solution of 4-{1-[3-(4-benzylphenoxy)propyl]-5-methyl-1H-pyrrol-2-yl}phenol (910 mg, 2.29 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (667 mg, 3.44 mmol) and triphenylphosphine (901 mg, 3.44 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (867 mg, 3.44 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 680 mg (yield: 51.5%) the mixture was extracted with ethyl acetate The extract was dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: To a solution of 4-[l-(3-decyloxyphenyl)-5-methyl-1H-pyrrol-2-yl]phenol (1.40 g, 3.45 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.00 g, 5.18 mmol) and triphenylphosphine (1.36 g, 5.18 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (1.31 g, 5.18 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 1.00 g (yield: 49.8%) the mixture was extracted with ethyl acetate The extract was dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: To a solution of 4-[l-(3-decyloxyphenyl)-5-methyl-1H-pyrrol-2-yl]phenol (1.40 g, 3.45 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.00 g, 5.18 mmol) and triphenylphosphine (1.36 g, 5.18 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (1.31 g, 5.18 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 1.00 g (yield: 49.8%) the mixture was extracted with ethyl acetate The extract was dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: To a solution of 4-(5-methyl-1-{2-[4-(4-pentylcyclohexylmethoxy)phenyl]ethyl}-1H-pyrrol-2-yl)phenol (830 mg, 1.81 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (526 mg, 2.71 mmol) and triphenylphosphine (711 mg, 2.71 mmol) in toluene (1 ml) was added 1,1′-(azodicarbonyl)dipiperidine (684 mg, 2.71 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 560 mg (yield: 48.7%) the mixture was extracted with ethyl acetate The extract was dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance

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

Procedure: A solution of 4-[1-(4-pentylphenylethyl)-5-methyl-1H-pyrrol-2-yl]phenol (1.82 g, 5.2 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.0 g, 5.1 mmol), 1,1′-(azodicarbonyl)dipiperidine (1.29 g, 5.1 mmol) and triphenylphosphine (1.34 g, 5.1 mmol) in toluene (5 ml) was stirred at 80° C. for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give the object compound as an oily substance. 660 mg, (yield 23%) extracted with ethyl acetate The extract was washed with saturated brine dried over magnesium sulfate anhydride The solvent was removed under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give the object compound as an oily substance

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

Procedure: A solution of 4-[1-(4-pentylphenylethyl)-5-methyl-1H-pyrrol-2-yl]phenol (1.82 g, 5.2 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.0 g, 5.1 mmol), 1,1′-(azodicarbonyl)dipiperidine (1.29 g, 5.1 mmol) and triphenylphosphine (1.34 g, 5.1 mmol) in toluene (5 ml) was stirred at 80° C. for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give the object compound as an oily substance. 660 mg, (yield 23%) extracted with ethyl acetate The extract was washed with saturated brine dried over magnesium sulfate anhydride The solvent was removed under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give the object compound as an oily substance

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

Procedure: A solution of 4-[5-methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenol (1.3 g, 3.6 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.05 g, 5.4 mmol), 1,1′-(azodicarbonyl)dipiperidine (1.36 g, 5.4 mmol) and triphenylphosphine (1.42 g, 5.4 mmol) in toluene (40 ml) was stirred at 80° C. for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the extract was washed with saturated brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give the object compound as an oily substance. 250 mg, (yield 13%) extracted with ethyl acetate the extract was washed with saturated brine dried over magnesium sulfate anhydride The solvent was removed under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give the object compound as an oily substance

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

Procedure: A solution of 4-[5-methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenol (1.3 g, 3.6 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.05 g, 5.4 mmol), 1,1′-(azodicarbonyl)dipiperidine (1.36 g, 5.4 mmol) and triphenylphosphine (1.42 g, 5.4 mmol) in toluene (40 ml) was stirred at 80° C. for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the extract was washed with saturated brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give the object compound as an oily substance. 250 mg, (yield 13%) extracted with ethyl acetate the extract was washed with saturated brine dried over magnesium sulfate anhydride The solvent was removed under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give the object compound as an oily substance

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

Procedure: A solution of 4-{1-[3-(4-butylphenyl)propan-1-yl]-5-methyl-1H-pyrrol-2-yl}phenol (880 mg, 2.53 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (492 mg, 2.53 mmol), triphenylphosphine (665 mg, 2.54 mmol) and diethyl azodicarboxylate (442 mg, 2.54 mmol) in toluene (30 ml) was refluxed for 20 hours under heating. The residue was poured into water, extracted with ethyl acetate, washed with saturated brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the object compound as an oily substance. 440 mg (yield: 33%) under heating extracted with ethyl acetate washed with saturated brine dried over magnesium sulfate anhydride The solvent was removed under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the object compound as an oily substance