ethyl (E)-5-phenylpent-2-enoate

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

Procedure: A solution of the intermediate 32.1 from above in 1:1 aqueous 1N LiOH:THF (250 mL) was refluxed for 18 h. It was then cooled to room temperature and washed with ethylacetate (2×200 mL). The aqueous was acidified to pH2 by the addition of conc. HCl, and extracted with ethylacetate (3×200 mL). These last organic extracts were combined, dried with MgSO4 and concentrated to afford the intermediate trans-5-phenyl-2-pentenoic acid (32.2). washed with ethylacetate (2×200 mL) The aqueous was acidified to pH2 by the addition of conc. HCl extracted with ethylacetate (3×200 mL) dried with MgSO4 concentrated

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

Procedure: A solution of the intermediate 32.1 from above in 1:1 aqueous 1N LiOH:THF (250 mL) was refluxed for 18 h. It was then cooled to room temperature and washed with ethylacetate (2×200 mL). The aqueous was acidified to pH2 by the addition of conc. HCl, and extracted with ethylacetate (3×200 mL). These last organic extracts were combined, dried with MgSO4 and concentrated to afford the intermediate trans-5-phenyl-2-pentenoic acid (32.2). washed with ethylacetate (2×200 mL) The aqueous was acidified to pH2 by the addition of conc. HCl extracted with ethylacetate (3×200 mL) dried with MgSO4 concentrated

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

Procedure: A solution of dihydrocinnamaldehyde (6.73 g, 50.2 mmol) and (carboethoxymethylene)triphenylphosphorane (17.84 g, 50.2 mmol) in toluene (250 mL) was refluxed for 18 h. It was then cooled to r.t. and concentrated in vacuo. The residue was taken up in ether (250 mL) and the triphenylphosphine oxide was filtered off. The filtrate was concentrated to afford the intermediate trans-ethyl-(5-phenyl)-2-pentenoate (32.1). concentrated in vacuo the triphenylphosphine oxide was filtered off The filtrate was concentrated

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

Procedure: A solution of the intermediate 32.1 from above in 1:1 aqueous 1 N LiOH:THF (250 mL) was refluxed for 18 h. It was then cooled to room temperature and washed with ethylacetate (2×200 mL). The aqueous was acidified to pH2 by the addition of conc. HCl, and extracted with ethylacetate (3×200 mL). These last organic extracts were combined, dried r with MgSO4 and concentrated to afford the intermediate trans-5-phenyl-2-pentenoic acid (32.2). washed with ethylacetate (2×200 mL) The aqueous was acidified to pH2 by the addition of conc. HCl extracted with ethylacetate (3×200 mL) dried r with MgSO4 concentrated

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

Procedure: A solution of the intermediate 32.1 from above in 1:1 aqueous 1 N LiOH:THF (250 mL) was refluxed for 18 h. It was then cooled to room temperature and washed with ethylacetate (2×200 mL). The aqueous was acidified to pH2 by the addition of conc. HCl, and extracted with ethylacetate (3×200 mL). These last organic extracts were combined, dried r with MgSO4 and concentrated to afford the intermediate trans-5-phenyl-2-pentenoic acid (32.2). washed with ethylacetate (2×200 mL) The aqueous was acidified to pH2 by the addition of conc. HCl extracted with ethylacetate (3×200 mL) dried r with MgSO4 concentrated

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

Procedure: A solution of dihydrocinnamaldehyde (6.73 g, 50.2 mmol) and (carboethoxymethylene)triphenylphosphorane (17.84 g, 50.2 mmol) in toluene (250 mL) was refluxed for 18 h. It was then cooled to r.t and concentrated in vacuo. The residue was taken up in ether (250 mL) and the triphenylphosphine oxide was filtered off. The filtrate was concentrated to afford the intermediate trans-ethyl-(5-phenyl)-2-pentenoate (32.1). It was then cooled concentrated in vacuo the triphenylphosphine oxide was filtered off The filtrate was concentrated

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

Procedure: A solution of dihydrocinnamaldehyde (6.73 g, 50.2 mmol) and (carboethoxymethylene)triphenylphosphorane (17.84 g, 50.2 mmol) in toluene (250 mL) was refluxed for 18 h. It was then cooled to r.t and concentrated in vacuo. The residue was taken up in ether (250 mL) and the triphenylphosphine oxide was filtered off. The filtrate was concentrated to afford the intermediate trans-ethyl-(5-phenyl)-2-pentenoate (32.1). It was then cooled concentrated in vacuo the triphenylphosphine oxide was filtered off The filtrate was concentrated

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

Procedure: A solution of (E)-ethyl 5-phenylpent-2-enoate (732 mg) in dry toluene (5 ml) was cooled to −78° C. DIBAL-H (1 M in hexanes, 7.17 ml) was added dropwise and the mixture was stirred for 3 h. A second portion of DIBAL-H (1 M in hexanes, 0.717 ml) was added and stirring was continued for another 3 h. The mixture was allowed to warm-up to RT and hydrolyzed with 1 M aqueous HCl (5 ml). Additional 3M aqueous HCl was added until pH=1 and the aqueous layer was extracted with EtOAc (3×). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was dissolved in dichloromethane (5 ml) and TEMPO (28.0 mg), potassium bromide (42.6 mg) and water (5 ml) were added. Aqueous sodium hypochlorite solution (13%, 1.642 ml) was added dropwise. The mixture was stirred at room temperature for 15 h. After phase separation the aqueous layer was extracted with CH2Cl2. The combined organic layer was washed with 1 M HCl, water and brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography to yield a slightly orange oil. stirring was continued for another 3 h the aqueous layer was extracted with EtOAc (3×) The combined organic layer was washed with brine dried over Na2SO4 concentrated The crude product was dissolved in dichloromethane (5 ml) TEMPO (28.0 mg), potassium bromide (42.6 mg) and water (5 ml) were added Aqueous sodium hypochlorite solution (13%, 1.642 ml) was added dropwise The mixture was stirred at room temperature for 15 h After phase separation the aqueous layer was extracted with CH2Cl2 The combined organic layer was washed with 1 M HCl, water and brine dried over Na2SO4 concentrated The crude product was purified by flash column chromatography to yield a slightly orange oil

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (60% wt., 181 mg) was suspended in dry tetrahydrofuran (5 ml) and cooled to 0° C. Triethyl phosphonoacetate (896 μl) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min. After cooling to −78° C. 3-phenylpropionaldehyde (500 μl) was added dropwise. The reaction mixture was stirred at this temperature for 1 h. The reaction mixture was allowed to warm-up to room temperature, hydrolyzed with water/THF, poured into water and the aqueous layer was extracted twice with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The crude was purified by flash column chromatography. After cooling to −78° C The reaction mixture was stirred at this temperature for 1 h the aqueous layer was extracted twice with EtOAc The combined organic layer was washed with brine dried over Na2SO4 concentrated The crude was purified by flash column chromatography

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

Procedure: A solution of the intermediate 32.1 from above in 1:1 aqueous 1N LiOH:THF (250 mL) was refluxed for 18 h. It was then cooled to room temperature and washed with ethylacetate (2×200 mL). The aqueous was acidified to pH2 by the addition of conc. HCl, and extracted with ethylacetate (3×200 mL). These last organic extracts were combined, dried with MgSO4 and concentrated to afford the intermediate trans-5-phenyl-2-pentenoic acid (32.2). washed with ethylacetate (2×200 mL) The aqueous was acidified to pH2 by the addition of conc. HCl extracted with ethylacetate (3×200 mL) dried with MgSO4 concentrated

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

Procedure: A solution of dihydrocinnamaldehyde (6.73 g, 50.2 mmol) and (carboethoxymethylene)triphenylphosphorane (17.84 g, 50.2 mmol) in toluene (250 mL) was refluxed for 18 h. It was then cooled to r.t. and concentrated in vacuo. The residue was taken up in ether (250 mL) and the triphenylphosphine oxide was filtered off. The filtrate was concentrated to afford the intermediate trans-ethyl-(5-phenyl)-2-pentenoate (32.1). concentrated in vacuo the triphenylphosphine oxide was filtered off The filtrate was concentrated