methyl 3-(4-hydroxyphenyl)hex-4-ynoate

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: To a 250 mL RB flask fitted with magnetic stirrer was charged with 30 mL of acetonitrile. To the stirred solvent were added methyl 3-(4-hydroxyphenyl)hex-4-ynoate (3.8 g, 17.4 mmol), potassium carbonate (7.2 g, 52.2 mmol). The reaction mixture was brought to 0° C., was added benzyl bromide (4.47 g, 1.5 mmol) in acetonitrile (20 mL) drop wise and stirred at room temperature for 16 h. The reaction mixture was concentrated to distill off the solvent. Water (20 mL) was added and extracted with ethyl acetate (60 mL). The organic layer was washed with water (20 mL) and saturated brine solution (20 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as elutants to obtain product (4.2 g, yield: 78.35%). To a 250 mL RB flask fitted with magnetic stirrer was brought to 0° C. The reaction mixture was concentrated to distill off the solvent Water (20 mL) was added extracted with ethyl acetate (60 mL) The organic layer was washed with water (20 mL) and saturated brine solution (20 mL) The organic layer was dried over anhydrous Na2SO4 the solvent was removed under reduced pressure The crude material was purified by silica gel column chromatography

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

Procedure: To a 250 mL RB flask fitted with magnetic stirrer was charged with 30 mL of acetonitrile. To the stirred solvent were added methyl 3-(4-hydroxyphenyl)hex-4-ynoate (3.8 g, 17.4 mmol), potassium carbonate (7.2 g, 52.2 mmol). The reaction mixture was brought to 0° C., was added benzyl bromide (4.47 g, 1.5 mmol) in acetonitrile (20 mL) drop wise and stirred at room temperature for 16 h. The reaction mixture was concentrated to distill off the solvent. Water (20 mL) was added and extracted with ethyl acetate (60 mL). The organic layer was washed with water (20 mL) and saturated brine solution (20 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as elutants to obtain product (4.2 g, yield: 78.35%). To a 250 mL RB flask fitted with magnetic stirrer was brought to 0° C. The reaction mixture was concentrated to distill off the solvent Water (20 mL) was added extracted with ethyl acetate (60 mL) The organic layer was washed with water (20 mL) and saturated brine solution (20 mL) The organic layer was dried over anhydrous Na2SO4 the solvent was removed under reduced pressure The crude material was purified by silica gel column chromatography

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

Procedure: Compound 85 was synthesized from (4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.2 g, 0.74 mmol) and methyl 3-(4-hydroxyphenyl)hex-4-ynoate (0.16 g, 0.74 mmol) by following the procedure described in scheme 28 (0.03 g, yield: 20.59%); Purity: 98.37%.

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

Procedure: Analogously to example 1, 2-chloro-4-(1-hydroxymethylcyclopropylmethoxy)benzonitrile and methyl 3-(4-hydroxyphenyl)hex-4-ynoate were used to obtain 3-{4-[1-(3-chloro-4-cyanophenoxymethyl)cyclopropylmethoxy]phenyl}hex-4-ynoic acid.

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

Procedure: Analogously to example 1, cyclobutane-1,1-diyldimethanol, phenol and methyl 3-(4-hydroxyphenyl)hex-4-ynoate were used to obtain 3-[4-(1-phenoxymethylcyclobutylmethoxy)phenyl]hex-4-ynoic acid.

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

Procedure: Analogously to example 1, cyclobutane-1,1-diyldimethanol, 3-methylphenol and methyl 3-(4-hydroxyphenyl)hex-4-ynoate were used to obtain 3-[4-(1-m-tolyloxymethylcyclobutylmethoxy)phenyl]hex-4-ynoic acid.

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

Procedure: Analogously to example 1, cyclobutane-1,1-diyldimethanol, 3-methylphenol and methyl 3-(4-hydroxyphenyl)hex-4-ynoate were used to obtain 3-[4-(1-m-tolyloxymethylcyclobutylmethoxy)phenyl]hex-4-ynoic acid.

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

Procedure: Analogously to example 1, cyclobutane-1,1-diyldimethanol, 4-hydroxybenzotrifluoride and methyl 3-(4-hydroxyphenyl)hex-4-ynoate were used to obtain 3-{4-[1-(4-trifluoromethylphenoxymethyl)cyclobutylmethoxy]phenyl}hex-4-ynoic acid.

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

Procedure: Analogously to example 1, cyclobutane-1,1-diyldimethanol, 3-tert-butylphenol and methyl 3-(4-hydroxyphenyl)hex-4-ynoate were used to obtain 3-{4-[1-(3-tert-butylphenoxymethyl)cyclobutylmethoxy]phenyl}hex-4-ynoic acid.