ethyl 3-naphthalen-1-ylpropanoate

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

Procedure: To a suspension of LiAlH4 (1.91 g, 50.4 mmol) in anhydrous ether (50 mL) was added dropwise a solution of 8 (11.5 g, 50.4 mmol) in ether (50 mL) over 30 minutes at 0° C. under argon and then the mixture was stirred at room temperature (overnight). The reaction mixture was cooled to 0° C. and quenched by slow (30 minutes addition of H2O (7.2 mL, 0.4 mol), then the mixture was stirred at 0° C. (1 h). Solid was removed by filtration washed with ether, then the combined ether solution was dried (Na2SO4) and taken to dryness, yielding 9 as an oil70 (9.36 g, 100%). 1H NMR (CDCl3) δ 8.08 (1H, dd, J=2.4, 7.4 Hz), 7.88 (1H, m), 7.74 (1H, d, J=7.6 Hz), 7.34˜7.57 (4H, m), 3.76 (2H, t, J=6.4 Hz), 3.20 (2H, t, J=7.5 Hz), 2.05 (2H, m), 1.75 (1H, brs). The reaction mixture was cooled to 0° C. quenched by slow ( the mixture was stirred at 0° C. (1 h) Solid was removed by filtration washed with ether the combined ether solution was dried (Na2SO4) yielding 9 as an oil70 (9.36 g, 100%)

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

Procedure: A solution of 7 (12 g, 53.1 mmol) in 95% EtOH (180 mL) was hydrogenated over 10% Pd.C (600 mg) at room temperature using an H2 filled balloon (overnight). The reaction mixture was filtered and taken to dryness to give a 8 as a clear oil80 (11.9 g, 98%). 1H NMR (CDCl3) δ 8.05 (1H, d, J=7.8 Hz), 7.86 (1H, dd, J=2.7, 7.6 Hz), 7.75 (1H, d, J=7.6 Hz), 7.35˜7.58 (4H, m), 4.17 (2H, q, J=7.1 Hz), 3.44 (2H, t, J=8.1 Hz), 2.77 (2H, t, J=8.3 Hz), 1.26 93H, t, J=7.1 Hz). at room temperature an H2 filled balloon (overnight) The reaction mixture was filtered to give a 8 as a clear oil80 (11.9 g, 98%)

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

Procedure: Under a nitrogen atmosphere, a mixture of 1.3 grams (0.033 mole) of lithium aluminum hydride in 40 mL of diethyl ether was stirred for one hour. The mixture was then cooled, and a solution of 10.0 grams (0.044 mole) of ethyl 3-(naphth-1-yl)propanoate in 35 mL of diethyl ether was added dropwise at a rate to keep the reaction mixture temperature below 25° C. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it was stirred for one hour. The reaction mixture was again cooled, and 50 mL of ethyl acetate was added to destroy excess lithium aluminum hydride. After this time 30 mL of an aqueous 10% sodium hydroxide solution was added dropwise. The reaction mixture was then acidified with aqueous 6N hydrochloric acid, and then it was poured into 300 mL of water. The organic layer was separated, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 8.2 grams of 3-(naphth-1-yl)propanol. The NMR spectrum was consistent with the proposed structure. The mixture was then cooled the reaction mixture temperature below 25° C Upon completion of addition was stirred for one hour The reaction mixture was again cooled to destroy excess lithium aluminum hydride After this time 30 mL of an aqueous 10% sodium hydroxide solution was added dropwise it was poured into 300 mL of water The organic layer was separated dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: Under a nitrogen atmosphere, a mixture of 1.3 grams (0.033 mole) of lithium aluminum hydride in 40 mL of diethyl ether was stirred for one hour. The mixture was then cooled, and a solution of 10.0 grams (0.044 mole) of ethyl 3-(naphth-1-yl)propanoate in 35 mL of diethyl ether was added dropwise at a rate to keep the reaction mixture temperature below 25° C. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it was stirred for one hour. The reaction mixture was again cooled, and 50 mL of ethyl acetate was added to destroy excess lithium aluminum hydride. After this time 30 mL of an aqueous 10% sodium hydroxide solution was added dropwise. The reaction mixture was then acidified with aqueous 6N hydrochloric acid, and then it was poured into 300 mL of water. The organic layer was separated, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 8.2 grams of 3-(naphth-1-yl)propanol. The NMR spectrum was consistent with the proposed structure. The mixture was then cooled the reaction mixture temperature below 25° C Upon completion of addition was stirred for one hour The reaction mixture was again cooled to destroy excess lithium aluminum hydride After this time 30 mL of an aqueous 10% sodium hydroxide solution was added dropwise it was poured into 300 mL of water The organic layer was separated dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: A stirred solution of 50 grams (0.25 mole) of 3-(naphth-1-yl)propanoic acid and 20 drops (catalyst) of concentrated sulfuric acid in 250 mL of ethanol was heated at reflux for about 24 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in diethyl ether, and the solution was washed with two 150 mL portions of an aqueous solution saturated with sodium bicarbonate and then with 150 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 56.0 grams of ethyl 3-(naphth-1-yl)propanoate. The NMR spectrum was consistent with the proposed structure. at reflux for about 24 hours After this time the reaction mixture was concentrated under reduced pressure to a residue The residue was dissolved in diethyl ether the solution was washed with two 150 mL portions of an aqueous solution saturated with sodium bicarbonate The organic layer was dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: To a solution of ethyl (2E)-3-(1-naphthyl)propenoate (37.6 g, 166 mmol) in ethanol (500 ml) was added 10% palladium carbon (4 g) and the mixture was stirred under hydrogen atmosphere for 5 hours. The insoluble matter was filtered out and the filtrate was concentrated to give the object compound as an oily substance. 37.7 g (yield: 99.7%) The insoluble matter was filtered out the filtrate was concentrated to give the object compound as an oily substance

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

Procedure: A mixture of ethyl 3-(1-naphthyl)propionate (18.01 g) and ethyl formate (8.88 g) was added to a suspension of sodium hydride (57% dispersion in oil, 4.43 g) in 1,2-dimethoxyethane stirred at 5°, and the mixture was stirred at 5° for one hour and allowed to warm to room temperature. Water (300 ml) was added and the mixture was extracted with chloroform and the residual aqueous phase adjusted to pH 4 with hydrochloric acid: the mixture was extracted with ether and the extracts evaporated to give ethyl 2-formyl-3-(1-naphthyl)-propionate (16.05 g) as an oil. the mixture was stirred at 5° for one hour the mixture was extracted with chloroform the mixture was extracted with ether the extracts evaporated

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

Procedure: A mixture of ethyl 3-(1-naphthyl)propionate (18.01 g) and ethyl formate (8.88 g) was added to a suspension of sodium hydride (57% dispersion in oil, 4.43 g) in 1,2-dimethoxyethane stirred at 5°, and the mixture was stirred at 5° for one hour and allowed to warm to room temperature. Water (300 ml) was added and the mixture was extracted with chloroform and the residual aqueous phase adjusted to pH 4 with hydrochloric acid: the mixture was extracted with ether and the extracts evaporated to give ethyl 2-formyl-3-(1-naphthyl)-propionate (16.05 g) as an oil. the mixture was stirred at 5° for one hour the mixture was extracted with chloroform the mixture was extracted with ether the extracts evaporated

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

Procedure: Under a nitrogen atmosphere, a mixture of 1.3 grams (0.033 mole) of lithium aluminum hydride in 40 mL of diethyl ether was stirred for one hour. The mixture was then cooled, and a solution of 10.0 grams (0.044 mole) of ethyl 3-(naphth-1-yl)propanoate in 35 mL of diethyl ether was added dropwise at a rate to keep the reaction mixture temperature below 25° C. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it was stirred for one hour. The reaction mixture was again cooled, and 50 mL of ethyl acetate was added to destroy excess lithium aluminum hydride. After this time 30 mL of an aqueous 10% sodium hydroxide solution was added dropwise. The reaction mixture was then acidified with aqueous 6N hydrochloric acid, and then it was poured into 300 mL of water. The organic layer was separated, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 8.2 grams of 3-(naphth-1-yl)propanol. The NMR spectrum was consistent with the proposed structure. The mixture was then cooled the reaction mixture temperature below 25° C Upon completion of addition was stirred for one hour The reaction mixture was again cooled to destroy excess lithium aluminum hydride After this time 30 mL of an aqueous 10% sodium hydroxide solution was added dropwise it was poured into 300 mL of water The organic layer was separated dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: A stirred solution of 50 grams (0.25 mole) of 3-(naphth-1-yl) propanoic acid and 20 drops (catalyst) of concentrated sulfuric acid in 250 mL of ethanol was heated at reflux for about 24 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in diethyl ether, and the solution was washed with two 150 mL portions of an aqueous solution saturated with sodium bicarbonate and then with 150 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 56.0 grams of ethyl 3-(naphth-1-yl)propanoate. The NMR spectrum was consistent with the proposed structure. at reflux for about 24 hours After this time the reaction mixture was concentrated under reduced pressure to a residue The residue was dissolved in diethyl ether the solution was washed with two 150 mL portions of an aqueous solution saturated with sodium bicarbonate The organic layer was dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: A stirred solution of 50 grams (0.25 mole) of 3-(naphth-1-yl) propanoic acid and 20 drops (catalyst) of concentrated sulfuric acid in 250 mL of ethanol was heated at reflux for about 24 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was dissolved in diethyl ether, and the solution was washed with two 150 mL portions of an aqueous solution saturated with sodium bicarbonate and then with 150 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 56.0 grams of ethyl 3-(naphth-1-yl)propanoate. The NMR spectrum was consistent with the proposed structure. at reflux for about 24 hours After this time the reaction mixture was concentrated under reduced pressure to a residue The residue was dissolved in diethyl ether the solution was washed with two 150 mL portions of an aqueous solution saturated with sodium bicarbonate The organic layer was dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: To a suspension of LiAlH4 (1.91 g, 50.4 mmol) in anhydrous ether (50 mL) was added dropwise a solution of 8 (11.5 g, 50.4 mmol) in ether (50 mL) over 30 minutes at 0° C. under argon and then the mixture was stirred at room temperature (overnight). The reaction mixture was cooled to 0° C. and quenched by slow (30 minutes addition of H2O (7.2 mL, 0.4 mol), then the mixture was stirred at 0° C. (1 h). Solid was removed by filtration washed with ether, then the combined ether solution was dried (Na2SO4) and taken to dryness, yielding 9 as an oil70 (9.36 g, 100%). 1H NMR (CDCl3) δ 8.08 (1H, dd, J=2.4, 7.4 Hz), 7.88 (1H, m), 7.74 (1H, d, J=7.6 Hz), 7.34˜7.57 (4H, m), 3.76 (2H, t, J=6.4 Hz), 3.20 (2H, t, J=7.5 Hz), 2.05 (2H, m), 1.75 (1H, brs). The reaction mixture was cooled to 0° C. quenched by slow ( the mixture was stirred at 0° C. (1 h) Solid was removed by filtration washed with ether the combined ether solution was dried (Na2SO4) yielding 9 as an oil70 (9.36 g, 100%)