ethyl 3-(furan-3-yl)propanoate

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

Procedure: To a suspension of 1.05 g (27.6 mmol) of lithium aluminum hydride in 100 ml of ether, a solution of 3.090 g (18.37 mmol) of ethyl 3-(3-furyl)propionate in 20 ml of ether was added dropwise under ice-cooling, followed by stirring at room temperature for 1 hour. To decompose the excess lithium aluminum hydride, ethyl acetate was added dropwise to the reaction mixture under ice-cooling; subsequently, water was added until a white precipitate formed. The white precipitate was filtered using Celite and washed with ethyl acetate 3 times. The combined filtrate was evaporated under reduced pressure. The obtained crude 3-(3-furyl)propanol was used for the next reaction without purification. cooling was added dropwise to the reaction mixture under ice- cooling formed The white precipitate was filtered washed with ethyl acetate 3 times The combined filtrate was evaporated under reduced pressure

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

Procedure: To a solution of 8.186 g (49.26 mmol) of ethyl (E)-3-(3-furyl)acrylate, 24.7 g (493 mmol) of hydrazine monohydrate, 5 ml of acetic acid and 5 ml of saturated aqueous copper sulfide in 500 ml of ethanol, a solution of 52.7 g (246 mmol) of sodium periodate in 300 ml of water was added dropwise over a period of 1 hour, followed by stirring at room temperature for 1 day. The reaction mixture was extracted with ether 3 times. The combined organic layer was washed with dilute hydrochloric acid and then aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to yield the desired product. The reaction mixture was extracted with ether 3 times The combined organic layer was washed with dilute hydrochloric acid aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)

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

Procedure: To a suspension of 1.05 g (27.6 mmol) of lithium aluminum hydride in 100 ml of ether, a solution of 3.090 g (18.37 mmol) of ethyl 3-(3-furyl)propionate in 20 ml of ether was added dropwise under ice-cooling, followed by stirring at room temperature for 1 hour. To decompose the excess lithium aluminum hydride, ethyl acetate was added dropwise to the reaction mixture under ice-cooling; subsequently, water was added until a white precipitate formed. The white precipitate was filtered using Celite and washed with ethyl acetate 3 times. The combined filtrate was evaporated under reduced pressure. The obtained crude 3-(3-furyl)propanol was used for the next reaction without purification. cooling was added dropwise to the reaction mixture under ice- cooling formed The white precipitate was filtered washed with ethyl acetate 3 times The combined filtrate was evaporated under reduced pressure

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

Procedure: To a solution of 8.186 g (49.26 mmol) of ethyl (E)-3-(3-furyl)acrylate, 24.7 g (493 mmol) of hydrazine monohydrate, 5 ml of acetic acid and 5 ml of saturated aqueous copper sulfide in 500 ml of ethanol, a solution of 52.7 g (246 mmol) of sodium periodate in 300 ml of water was added dropwise over a period of 1 hour, followed by stirring at room temperature for 1 day. The reaction mixture was extracted with ether 3 times. The combined organic layer was washed with dilute hydrochloric acid and then aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to yield the desired product. The reaction mixture was extracted with ether 3 times The combined organic layer was washed with dilute hydrochloric acid aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)