3-(4-methoxyphenyl)propanamide

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

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

Procedure: Lithium aluminium hydride (0.01 mol) and tetrahydrofuran (500 ml) were placed in a 1 liter flask fitted with a soxhlet extractor, with 3-(4-methoxyphenyl)propanamide (0.056 mol) in the extraction thimble. The reaction was refluxed 3 hours, was cooled and water (3.5 ml) was carefully added. After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml), the mixture was filtered and concentrated. The crude product was distilled (Kugelrohr) to yield 4.4 g (48%) of a colorless oil which was stored under N2. The reaction was refluxed 3 hours was cooled After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml) the mixture was filtered concentrated The crude product was distilled (Kugelrohr)

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

Procedure: Lithium aluminium hydride (0.01 mol) and tetrahydrofuran (500 ml) were placed in a 1 liter flask fitted with a soxhlet extractor, with 3-(4-methoxyphenyl)propanamide (0.056 mol) in the extraction thimble. The reaction was refluxed 3 hours, was cooled and water (3.5 ml) was carefully added. After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml), the mixture was filtered and concentrated. The crude product was distilled (Kugelrohr) to yield 4.4 g (48%) of a colorless oil which was stored under N2. The reaction was refluxed 3 hours was cooled After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml) the mixture was filtered concentrated The crude product was distilled (Kugelrohr)

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

Procedure: 3-(4-methoxyphenyl)propionic acid amide (10.3 mg, 0.059 mmol) prepared in Reference Synthetic Example 3 was dissolved in tetrahydrofuran (500 μl) in nitrogen atmosphere, tetrakistriphenylphosphine palladium (1.4 mg, 0.0012 mmol) was added under cooling with ice, and a tetrahydrofuran solution of tri-n-butyltin hydride (20 μl, 0.074 mmol) was dropwise added. After stirring for 10 minutes, the solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the desired compound (E)-2-{tri(n-butyl)stannyl}-3-(4-methoxyphenyl)acrylamide (18.6 mg, 68%) as a colorless oily substance. was added under cooling with ice the solution was concentrated under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

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

Procedure: (4-methoxyphenyl)propionic acid (20.0 mg, 0.11 mmol) prepared in Reference Synthetic Example 2 was dissolved in tetrahydrofuran (500 μl) in nitrogen atmosphere, and triethylamine (17 μl, 0.12 mmol) and ethyl chloroformate (11 μl, 0.12 mmol) were dropwise added under cooling with ice, followed by stirring for 15 minutes. A 28% ammonia aqueous solution was dropwise added, followed by stirring for 5 minutes, and the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2 to 1:2) to give the desired compound 3-(4-methoxyphenyl)propionic acid amide (18.9 mg, 95%) as colorless needle crystals. were dropwise added under cooling with ice by stirring for 5 minutes extracted with ethyl acetate The organic layer was concentrated under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2 to 1:2)

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

Procedure: (4-methoxyphenyl)propionic acid (20.0 mg, 0.11 mmol) prepared in Reference Synthetic Example 2 was dissolved in tetrahydrofuran (500 μl) in nitrogen atmosphere, and triethylamine (17 μl, 0.12 mmol) and ethyl chloroformate (11 μl, 0.12 mmol) were dropwise added under cooling with ice, followed by stirring for 15 minutes. A 28% ammonia aqueous solution was dropwise added, followed by stirring for 5 minutes, and the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2 to 1:2) to give the desired compound 3-(4-methoxyphenyl)propionic acid amide (18.9 mg, 95%) as colorless needle crystals. were dropwise added under cooling with ice by stirring for 5 minutes extracted with ethyl acetate The organic layer was concentrated under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2 to 1:2)

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

Procedure: Lithium aluminium hydride (0.01 mol) and tetrahydrofuran (500 ml) were placed in a 1 liter flask fitted with a soxhlet extractor, with 3-(4-methoxyphenyl)propanamide (0.056 mol) in the extraction thimble. The reaction was refluxed 3 hours, was cooled and water (3.5 ml) was carefully added. After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml), the mixture was filtered and concentrated. The crude product was distilled (Kugelrohr) to yield 4.4 g (48%) of a colorless oil which was stored under N2. The reaction was refluxed 3 hours was cooled After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml) the mixture was filtered concentrated The crude product was distilled (Kugelrohr)

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

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

Procedure: Lithium aluminium hydride (0.01 mol) and tetrahydrofuran (500 ml) were placed in a 1 liter flask fitted with a soxhlet extractor, with 3-(4-methoxyphenyl)propanamide (0.056 mol) in the extraction thimble. The reaction was refluxed 3 hours, was cooled and water (3.5 ml) was carefully added. After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml), the mixture was filtered and concentrated. The crude product was distilled (Kugelrohr) to yield 4.4 g (48%) of a colorless oil which was stored under N2. The reaction was refluxed 3 hours was cooled After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml) the mixture was filtered concentrated The crude product was distilled (Kugelrohr)

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

Procedure: 3-(4-methoxyphenyl)propionic acid amide (10.3 mg, 0.059 mmol) prepared in Reference Synthetic Example 3 was dissolved in tetrahydrofuran (500 μl) in nitrogen atmosphere, tetrakistriphenylphosphine palladium (1.4 mg, 0.0012 mmol) was added under cooling with ice, and a tetrahydrofuran solution of tri-n-butyltin hydride (20 μl, 0.074 mmol) was dropwise added. After stirring for 10 minutes, the solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the desired compound (E)-2-{tri(n-butyl)stannyl}-3-(4-methoxyphenyl)acrylamide (18.6 mg, 68%) as a colorless oily substance. was added under cooling with ice the solution was concentrated under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

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

Procedure: (4-methoxyphenyl)propionic acid (20.0 mg, 0.11 mmol) prepared in Reference Synthetic Example 2 was dissolved in tetrahydrofuran (500 μl) in nitrogen atmosphere, and triethylamine (17 μl, 0.12 mmol) and ethyl chloroformate (11 μl, 0.12 mmol) were dropwise added under cooling with ice, followed by stirring for 15 minutes. A 28% ammonia aqueous solution was dropwise added, followed by stirring for 5 minutes, and the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2 to 1:2) to give the desired compound 3-(4-methoxyphenyl)propionic acid amide (18.9 mg, 95%) as colorless needle crystals. were dropwise added under cooling with ice by stirring for 5 minutes extracted with ethyl acetate The organic layer was concentrated under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2 to 1:2)

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

Procedure: Lithium aluminium hydride (0.01 mol) and tetrahydrofuran (500 ml) were placed in a 1 liter flask fitted with a soxhlet extractor, with 3-(4-methoxyphenyl)propanamide (0.056 mol) in the extraction thimble. The reaction was refluxed 3 hours, was cooled and water (3.5 ml) was carefully added. After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml), the mixture was filtered and concentrated. The crude product was distilled (Kugelrohr) to yield 4.4 g (48%) of a colorless oil which was stored under N2. The reaction was refluxed 3 hours was cooled After the mixture was sequentially extracted with 10% aqueous sodium hydroxide (3.5 ml) and water (10.5 ml) the mixture was filtered concentrated The crude product was distilled (Kugelrohr)