ethyl 3-(furan-2-yl)propanoate

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

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

Procedure: A cis/trans mixture of ethyl (E)-3-(2-furyl)prop-2-enoate (15.5 g, 93.27 mmol, 1 eq) was stirred in ethanol (120 ml) containing 10% palladium on charcoal (775 mg, 5% by w). The reaction mixture was stirred under hydrogen for 4 h. A further quantity of 10% Pd/C (775 mg, 5% by w) was added. The reaction was stirred under hydrogen for an additional 95 mins. The reaction was filtered and evaporated under reduced pressure. The crude product was purified by silica column chromatography eluting with 20% ethyl acetate in hexanes. The desired fractions were evaporated under reduced pressure and ethyl 3-(2-furyl)propanoate was obtained as a clear oil (3.69 g, 24% yield). The reaction was stirred under hydrogen for an additional 95 mins The reaction was filtered evaporated under reduced pressure The crude product was purified by silica column chromatography eluting with 20% ethyl acetate in hexanes The desired fractions were evaporated under reduced pressure

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

Procedure: Ethyl 3-(2-furyl)propionate was reacted with 1.1 equivalents ethyl formate and 1.0 equivalents sodium hydride in 1,2-dimethoxyethane at room temperature to give ethyl 2-formyl-3-(2-furyl)propionate as an oil in 75% yield.

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

Procedure: A cis/trans mixture of ethyl (E)-3-(2-furyl)prop-2-enoate (15.5 g, 93.27 mmol, 1 eq) was stirred in ethanol (120 ml) containing 10% palladium on charcoal (775 mg, 5% by w). The reaction mixture was stirred under hydrogen for 4 h. A further quantity of 10% Pd/C (775 mg, 5% by w) was added. The reaction was stirred under hydrogen for an additional 95 mins. The reaction was filtered and evaporated under reduced pressure. The crude product was purified by silica column chromatography eluting with 20% ethyl acetate in hexanes. The desired fractions were evaporated under reduced pressure and ethyl 3-(2-furyl)propanoate was obtained as a clear oil (3.69 g, 24% yield). The reaction was stirred under hydrogen for an additional 95 mins The reaction was filtered evaporated under reduced pressure The crude product was purified by silica column chromatography eluting with 20% ethyl acetate in hexanes The desired fractions were evaporated under reduced pressure

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

Procedure: A cis/trans mixture of ethyl (E)-3-(2-furyl)prop-2-enoate (15.5 g, 93.27 mmol, 1 eq) was stirred in ethanol (120 ml) containing 10% palladium on charcoal (775 mg, 5% by w). The reaction mixture was stirred under hydrogen for 4 h. A further quantity of 10% Pd/C (775 mg, 5% by w) was added. The reaction was stirred under hydrogen for an additional 95 mins. The reaction was filtered and evaporated under reduced pressure. The crude product was purified by silica column chromatography eluting with 20% ethyl acetate in hexanes. The desired fractions were evaporated under reduced pressure and ethyl 3-(2-furyl)propanoate was obtained as a clear oil (3.69 g, 24% yield). The reaction was stirred under hydrogen for an additional 95 mins The reaction was filtered evaporated under reduced pressure The crude product was purified by silica column chromatography eluting with 20% ethyl acetate in hexanes The desired fractions were evaporated under reduced pressure

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

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

Procedure: To a stirred solution of 2-(2'-carbethoxyethyl)furan (42.5 g.) in 750 ml. of methanol containing 53 g. of sodium carbonate at -25° C. is added a solution of 40.5 g. of bromine in 250 ml. of methanol during the course of 2.5 hours. The solution is stirred at room temperature for 30 minutes, diluted with brine, and extracted with diethyl ether. The extract is washed with brine, dried over magnesium sulfate, and concentrated. The residue is distilled to provide a light yellow liquid, b.p. 78°-84° C. (0.2 mm.), ν max 1740 (ester carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group). during the course of 2.5 hours extracted with diethyl ether The extract is washed with brine dried over magnesium sulfate concentrated The residue is distilled to provide a light yellow liquid, b.p. 78°-84° C. (0.2 mm.), ν max 1740 (ester carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group)

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

Procedure: To a stirred solution of 2-(2'-carbethoxyethyl)furan (42.5 g.) in 750 ml. of methanol containing 53 g. of sodium carbonate at -25° C. is added a solution of 40.5 g. of bromine in 250 ml. of methanol during the course of 2.5 hours. The solution is stirred at room temperature for 30 minutes, diluted with brine, and extracted with diethyl ether. The extract is washed with brine, dried over magnesium sulfate, and concentrated. The residue is distilled to provide a light yellow liquid, b.p. 78°-84° C. (0.2 mm.), ν max 1740 (ester carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group). during the course of 2.5 hours extracted with diethyl ether The extract is washed with brine dried over magnesium sulfate concentrated The residue is distilled to provide a light yellow liquid, b.p. 78°-84° C. (0.2 mm.), ν max 1740 (ester carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group)

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

Procedure: A mixture of ethyl 3-(2-furanyl)propionate (33.77 g) and ethyl formate (22.22 g) was added dropwise with stirring to a pre-cooled (0° C.) suspension of sodium hydride (50% in oil; 8.45 g) in dimethoxyethane (70 ml) maintaining the temperature below 0° C. throughout the addition. The reaction mixture was allowed to warm to room temperature then poured on to ice and water and extracted with ethyl acetate. The aqueous layer was acidified to pH 4 and re-extracted with ethyl acetate. These second ethyl acetate extracts were combined dried (MgSO4) and evaporated at reduced pressure to yield ethyl 3-(2-furanyl)-2-formylpropionate (19.0 g). was added dropwise a pre-cooled maintaining the temperature below 0° C. throughout the addition extracted with ethyl acetate re-extracted with ethyl acetate These second ethyl acetate extracts were combined dried (MgSO4) evaporated at reduced pressure

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

Procedure: A mixture of ethyl 3-(2-furanyl)acrylate (46.7 g) and conc. ammonium hydroxide solution (25 ml) was hydrogenated in the presence of Raney Nickel (500 mg) at 35° C. until a theoretical amount of hydrogen was taken up. The Raney Nickel was removed by filtering through diatomaceous earth and the filtrate was evaporated at reduced pressure to yield a brown oil. The oil was dissolved in ethyl acetate, washed with distilled water, dried (MgSO4) and the solvent evaporated at reduced pressure to yield ethyl 3-(2-furanyl)-propionate (33.77 g) as a brown oil. The Raney Nickel was removed by filtering through diatomaceous earth the filtrate was evaporated at reduced pressure to yield a brown oil washed with distilled water dried (MgSO4) the solvent evaporated at reduced pressure

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

Procedure: A mixture of ethyl 2-triphenylphosphoranylideneacetate (34.84 g, 100 mmol, 1 eq) and furan-2-carbaldehyde (9609 mg, 100 mmol, 1 eq) in anhydrous THF (200 ml) was stirred at room temperature for 24 h. The solvent was evaporated under reduced pressure and the residue triturated with ether to produce a brown solution and a precipitate. The solid was filtered, washed and removed. The filtrate was then evaporated. The product was purified by column chromatography on silica eluting with 0-20% ethyl acetate in hexanes. The desired fractions were evaporated to yield a cis/trans mixture of ethyl (E)-3-(2-furyl)prop-2-enoate as a pale yellow oil (NMR suggested mainly trans product) (15.5 g, 93%). b) A cis/trans mixture of ethyl (E)-3-(2-furyl)prop-2-enoate (15.5 g, 93.27 mmol, 1 eq) was stirred in ethanol (120 ml) containing 10% palladium on charcoal (775 mg, 5% by w). The reaction mixture was stirred under hydrogen for 4 h. A further quantity of 10% Pd/C (775 mg, 5% by w) was added. The reaction was stirred under hydrogen for an additional 95 mins. The reaction was filtered and evaporated under reduced pressure. The crude product was purified by silica column chromatography eluting with 20% ethyl acetate in hexanes. The desired fractions were evaporated under reduced pressure and ethyl 3-(2-furyl)propanoate was obtained as a clear oil (3.69 g, 24% yield). The solvent was evaporated under reduced pressure the residue triturated with ether to produce a brown solution The solid was filtered washed removed The filtrate was then evaporated The product was purified by column chromatography on silica eluting with 0-20% ethyl acetate in hexanes The desired fractions were evaporated to yield The reaction mixture was stirred under hydrogen for 4 h The reaction was stirred under hydrogen for an additional 95 mins The reaction was filtered evaporated under reduced pressure The crude product was purified by silica column chromatography eluting with 20% ethyl acetate in hexanes The desired fractions were evaporated under reduced pressure

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

Procedure: To a stirred solution of 2-(2'-carbethoxyethyl)furan (42.5 g.) in 750 ml. of methanol containing 53 g. of sodium carbonate at -25°C. is added a solution of 40.5 g. of bromine in 250 ml. of methanol during the course of 2.5 hours. The solution is stirred at room temperature for 30 minutes, diluted with brine, and extracted with diethyl ether. The extract is washed with brine, dried over magnesium sulfate, and concentrated. The residue is distilled to provide a light yellow liquid, b.p. 78°-84°C. (0.2 mm.), γ max 1740 (ester carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group). during the course of 2.5 hours extracted with diethyl ether The extract is washed with brine dried over magnesium sulfate concentrated The residue is distilled to provide a light yellow liquid, b.p. 78°-84°C. (0.2 mm.), γ max 1740 (ester carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group)