1-phenylpent-4-en-1-one

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

Procedure: A 1 L round bottomed flask was charged with 1-phenyl-4-penten-1-one (49.1 g, 307 mmol), THF (200 mL), and a stir bar, and cooled in an ice bath. Cyclopentadienyl magnesium chloride (330 mL of approximately 1 M solution in THF, 330 mmol) was added dropwise over 1 hour. The pale red solution was stirred overnight while warming to room temperature. The solution was then refluxed for 4.5 hours, during which time the red color intensified. After being stirred overnight at room temperature again, the solution was acidified by first adding 5.5 g of ammonium chloride in 100 mL of water, and then adding 50 mL of 1 M HCl. The product was extracted with pentane, and the pentane extracts were collected, washed with water, and dried over sodium sulfate. Elution through silica with heptane and concentration under vacuum afforded 38.6 g (55% isolated and purified yield) of the product 6-phenyl-6-(3-butenyl)fulvene as a red oil. cooled in an ice bath The solution was then refluxed for 4.5 hours, during which time the red color After being stirred overnight at room temperature again The product was extracted with pentane the pentane extracts were collected washed with water dried over sodium sulfate Elution through silica with heptane and concentration under vacuum afforded

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

Procedure: A sodium solution of alcohol was prepared by dissolving 33 g of sodium in 1000 mL of ethanol. To the warm solution, 260 mL of benzoyl-acetic acid-ethylester was added and then 130 mL of allyl bromide was slowly dropped into the solution. The mixture was refluxed for 4 hrs. and then the solid removed in a vacuum. The resulting solid was then combined in an aqueous solution of potassium hydroxide prepared by combining 145 g of potassium hydroxide with 500 mL of water. This mixture was heated under reflux for 4 hrs. The mixture was then neutralized and extracted three times with 150 mL of diethylether. The organic layer was separated, washed twice with water, and dried. The solvent was removed in a vacuum to produce a 98 percent yield of phenyl-(but-3-enyl) ketone. The mixture was refluxed for 4 hrs and then the solid removed in a vacuum prepared This mixture was heated under reflux for 4 hrs extracted three times with 150 mL of diethylether The organic layer was separated washed twice with water dried The solvent was removed in a vacuum

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

Procedure: A sodium solution of alcohol was prepared by dissolving 33 g of sodium in 1000 mL of ethanol. To the warm solution, 260 mL of benzoyl-acetic acid-ethylester was added and then 130 mL of allyl bromide was slowly dropped into the solution. The mixture was refluxed for 4 hrs. and then the solid removed in a vacuum. The resulting solid was then combined in an aqueous solution of potassium hydroxide prepared by combining 145 g of potassium hydroxide with 500 mL of water. This mixture was heated under reflux for 4 hrs. The mixture was then neutralized and extracted three times with 150 mL of diethylether. The organic layer was separated, washed twice with water, and dried. The solvent was removed in a vacuum to produce a 98 percent yield of phenyl-(but-3-enyl) ketone. The mixture was refluxed for 4 hrs and then the solid removed in a vacuum prepared This mixture was heated under reflux for 4 hrs extracted three times with 150 mL of diethylether The organic layer was separated washed twice with water dried The solvent was removed in a vacuum

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

Procedure: A 1 L round bottomed flask was charged with 1-phenyl-4-penten-1-one (49.1 g, 307 mmol), THF (200 mL), and a stir bar, and cooled in an ice bath. Cyclopentadienyl magnesium chloride (330 mL of approximately 1 M solution in THF, 330 mmol) was added dropwise over 1 hour. The pale red solution was stirred overnight while warming to room temperature. The solution was then refluxed for 4.5 hours, during which time the red color intensified. After being stirred overnight at room temperature again, the solution was acidified by first adding 5.5 g of ammonium chloride in 100 mL of water, and then adding 50 mL of 1 M HCl. The product was extracted with pentane, and the pentane extracts were collected, washed with water, and dried over sodium sulfate. Elution through silica with heptane and concentration under vacuum afforded 38.6 g (55% isolated and purified yield) of the product 6-phenyl-6-(3-butenyl)fulvene as a red oil. cooled in an ice bath The solution was then refluxed for 4.5 hours, during which time the red color After being stirred overnight at room temperature again The product was extracted with pentane the pentane extracts were collected washed with water dried over sodium sulfate Elution through silica with heptane and concentration under vacuum afforded

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

Procedure: Ethyl benzoylacetate (38.4 g, 0.2 mole, Aldrich) was added to a mixture of sodium ethoxide (13.6 g, 0.2 moles) in 200 mL ethanol. The mixture was stirred magnetically and slowly brought to reflux. After 30 minutes, the reaction mixture was cooled and allyl bromide (26.6 g, 0.22 moles, Aldrich) was added via a syringe with care (10 minutes), and the mixture was refluxed for another 2 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel and diluted with 300 mL saturated sodium bicarbonate and extracted with ether (200 mL×3). The combined ether layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation resulting in a brownish oil. Without further purification, the crude product was suspended in 250 mL 1 normal sodium hydroxide solution and brought to gentle reflux overnight. After cooling, the oil that floated on top was separated and was combine with the organic layer from the extractions that followed. The aqueous layer was acidified with 50% sulfuric acid to pH 1 and heated to reflux for 5 hours. The mixture was extracted with ethyl acetate (200 mL×3). The organic layer was dried over sodium sulfate and the solvent removed by rotary evaporation to yield a yellow oil. Yield: 19.7 g (61.5%) with boiling point 70-80° C. at 0.8 mmHg. 1H-NMR (CDCl3, δ): phenyl ring (7.97, d, 2H, 7.55, m, 1H, 7.4, m, 2H); vinyl group (5.8, m 2H, 5.1 q, 1H); 3.08 (t, 2H); 2.5 (m, 2H). See also, Vogel et al., Vogel's Textbook of Practical Organic Chemistry. Fifth Edition, revised by Furniss et al., 1989, Pearson Prentice Hall). to reflux the reaction mixture was cooled the mixture was refluxed for another 2 hours the mixture was transferred to a separatory funnel extracted with ether (200 mL×3) The combined ether layer was washed with brine dried over anhydrous magnesium sulfate The solvent was removed by rotary evaporation resulting in a brownish oil Without further purification to gentle reflux overnight After cooling was separated from the extractions that heated to reflux for 5 hours The mixture was extracted with ethyl acetate (200 mL×3) The organic layer was dried over sodium sulfate the solvent removed by rotary evaporation to yield a yellow oil

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

Procedure: A 1 L round bottomed flask was charged with 1-phenyl-4-penten-1-one (49.1 g, 307 mmol), THF (200 mL), and a stir bar, and cooled in an ice bath. Cyclopentadienyl magnesium chloride (330 mL of approximately 1 M solution in THF, 330 mmol) was added dropwise over 1 hour. The pale red solution was stirred overnight while warming to room temperature. The solution was then refluxed for 4.5 hours, during which time the red color intensified. After being stirred overnight at room temperature again, the solution was acidified by first adding 5.5 g of ammonium chloride in 100 mL of water, and then adding 50 mL of 1 M HCl. The product was extracted with pentane, and the pentane extracts were collected, washed with water, and dried over sodium sulfate. Elution through silica with heptane and concentration under vacuum afforded 38.6 g (55% isolated and purified yield) of the product 6-phenyl-6-(3-butenyl)fulvene as a red oil. cooled in an ice bath The solution was then refluxed for 4.5 hours, during which time the red color After being stirred overnight at room temperature again The product was extracted with pentane the pentane extracts were collected washed with water dried over sodium sulfate Elution through silica with heptane and concentration under vacuum afforded

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

Procedure: Ethyl benzoylacetate (38.4 g, 0.2 mole, Aldrich) was added to a mixture of sodium ethoxide (13.6 g, 0.2 moles) in 200 mL ethanol. The mixture was stirred magnetically and slowly brought to reflux. After 30 minutes, the reaction mixture was cooled and allyl bromide (26.6 g, 0.22 moles, Aldrich) was added via a syringe with care (10 minutes), and the mixture was refluxed for another 2 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel and diluted with 300 mL saturated sodium bicarbonate and extracted with ether (200 mL×3). The combined ether layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation resulting in a brownish oil. Without further purification, the crude product was suspended in 250 mL 1 normal sodium hydroxide solution and brought to gentle reflux overnight. After cooling, the oil that floated on top was separated and was combine with the organic layer from the extractions that followed. The aqueous layer was acidified with 50% sulfuric acid to pH 1 and heated to reflux for 5 hours. The mixture was extracted with ethyl acetate (200 mL×3). The organic layer was dried over sodium sulfate and the solvent removed by rotary evaporation to yield a yellow oil. Yield: 19.7 g (61.5%) with boiling point 70-80° C. at 0.8 mmHg. 1H-NMR (CDCl3, δ): phenyl ring (7.97, d, 2H, 7.55, m, 1H, 7.4, m, 2H); vinyl group (5.8, m 2H, 5.1 q, 1H); 3.08 (t, 2H); 2.5 (m, 2H). See also, Vogel et al., Vogel's Textbook of Practical Organic Chemistry. Fifth Edition, revised by Furniss et al., 1989, Pearson Prentice Hall). to reflux the reaction mixture was cooled the mixture was refluxed for another 2 hours the mixture was transferred to a separatory funnel extracted with ether (200 mL×3) The combined ether layer was washed with brine dried over anhydrous magnesium sulfate The solvent was removed by rotary evaporation resulting in a brownish oil Without further purification to gentle reflux overnight After cooling was separated from the extractions that heated to reflux for 5 hours The mixture was extracted with ethyl acetate (200 mL×3) The organic layer was dried over sodium sulfate the solvent removed by rotary evaporation to yield a yellow oil

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

Procedure: In 50 ml of toluene, 1.60 g of 4-pentenophenone, 2.13 g of pyrrolidine and 0.14 g of boron trifluoride etherate were dissolved. The mixture was refluxed for 46 hours using a Cope water separator and molecular sieve 4A as the dehydrating agent. After having distilled out the solvent under a reduced pressure, the residue was subjected to a distillation under a reduced pressure to obtain 1.68 g of the desired enamine (yield: 79%). The mixture was refluxed for 46 hours After having distilled out the solvent under a reduced pressure the residue was subjected to a distillation under a reduced pressure

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

Procedure: A sodium solution of alcohol was prepared by dissolving 33 g of sodium in 1000 mL of ethanol. To the warm solution, 260 mL of benzoyl-acetic acid-ethylester was added and then 130 mL of allyl bromide was slowly dropped into the solution. The mixture was refluxed for 4 hrs. and then the solid removed in a vacuum. The resulting solid was then combined in an aqueous solution of potassium hydroxide prepared by combining 145 g of potassium hydroxide with 500 mL of water. This mixture was heated under reflux for 4 hrs. The mixture was then neutralized and extracted three times with 150 mL of diethylether. The organic layer was separated, washed twice with water, and dried. The solvent was removed in a vacuum to produce a 98 percent yield of phenyl-(but-3-enyl)ketone. The mixture was refluxed for 4 hrs and then the solid removed in a vacuum prepared This mixture was heated under reflux for 4 hrs extracted three times with 150 mL of diethylether The organic layer was separated washed twice with water dried The solvent was removed in a vacuum

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

Procedure: A sodium solution of alcohol was prepared by dissolving 33 g of sodium in 1000 mL of ethanol. To the warm solution, 260 mL of benzoyl-acetic acid-ethylester was added and then 130 mL of allyl bromide was slowly dropped into the solution. The mixture was refluxed for 4 hrs. and then the solid removed in a vacuum. The resulting solid was then combined in an aqueous solution of potassium hydroxide prepared by combining 145 g of potassium hydroxide with 500 mL of water. This mixture was heated under reflux for 4 hrs. The mixture was then neutralized and extracted three times with 150 mL of diethylether. The organic layer was separated, washed twice with water, and dried. The solvent was removed in a vacuum to produce a 98 percent yield of phenyl-(but-3-enyl) ketone. The mixture was refluxed for 4 hrs and then the solid removed in a vacuum prepared This mixture was heated under reflux for 4 hrs extracted three times with 150 mL of diethylether The organic layer was separated washed twice with water dried The solvent was removed in a vacuum

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

Procedure: A sodium solution of alcohol was prepared by dissolving 33 g of sodium in 1000 mL of ethanol. To the warm solution, 260 mL of benzoyl-acetic acid-ethylester was added and then 130 mL of allyl bromide was slowly dropped into the solution. The mixture was refluxed for 4 hrs. and then the solid removed in a vacuum. The resulting solid was then combined in an aqueous solution of potassium hydroxide prepared by combining 145 g of potassium hydroxide with 500 mL of water. This mixture was heated under reflux for 4 hrs. The mixture was then neutralized and extracted three times with 150 mL of diethylether. The organic layer was separated, washed twice with water, and dried. The solvent was removed in a vacuum to produce a 98 percent yield of phenyl-(but-3-enyl) ketone. The mixture was refluxed for 4 hrs and then the solid removed in a vacuum prepared This mixture was heated under reflux for 4 hrs extracted three times with 150 mL of diethylether The organic layer was separated washed twice with water dried The solvent was removed in a vacuum

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

Procedure: Ethyl benzoylacetate (38.4 g, 0.2 mole, Aldrich) was added to a mixture of sodium ethoxide (13.6 g, 0.2 moles) in 200 mL ethanol. The mixture was stirred magnetically and slowly brought to reflux. After 30 minutes, the reaction mixture was cooled and allyl bromide (26.6 g, 0.22 moles, Aldrich) was added via a syringe with care (10 minutes), and the mixture was refluxed for another 2 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel and diluted with 300 mL saturated sodium bicarbonate and extracted with ether (200 mL×3). The combined ether layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation resulting in a brownish oil. Without further purification, the crude product was suspended in 250 mL 1 normal sodium hydroxide solution and brought to gentle reflux overnight. After cooling, the oil that floated on top was separated and was combine with the organic layer from the extractions that followed. The aqueous layer was acidified with 50% sulfuric acid to pH 1 and heated to reflux for 5 hours. The mixture was extracted with ethyl acetate (200 mL×3). The organic layer was dried over sodium sulfate and the solvent removed by rotary evaporation to yield a yellow oil. Yield: 19.7 g (61.5%) with boiling point 70-80° C. at 0.8 mmHg. 1H-NMR (CDCl3, δ): phenyl ring (7.97, d, 2H, 7.55, m, 1H, 7.4, m, 2H); vinyl group (5.8, m 2H, 5.1 q, 1H); 3.08 (t, 2H); 2.5 (m, 2H). See also, Vogel et al., Vogel's Textbook of Practical Organic Chemistry. Fifth Edition, revised by Furniss et al., 1989, Pearson Prentice Hall). to reflux the reaction mixture was cooled the mixture was refluxed for another 2 hours the mixture was transferred to a separatory funnel extracted with ether (200 mL×3) The combined ether layer was washed with brine dried over anhydrous magnesium sulfate The solvent was removed by rotary evaporation resulting in a brownish oil Without further purification to gentle reflux overnight After cooling was separated from the extractions that heated to reflux for 5 hours The mixture was extracted with ethyl acetate (200 mL×3) The organic layer was dried over sodium sulfate the solvent removed by rotary evaporation to yield a yellow oil