4-phenylpentan-2-one

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

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

Procedure: As in Example 1 except using 4-phenyl-2-pentanone instead of benzyl acetone, and iso butyryl chloride instead of benzoyl chloride b.p. 130-134 (0.4 mm).

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

Procedure: As in Example 1 except using 4-phenyl-2-pentanone instead of benzyl acetone, and iso butyryl chloride instead of benzoyl chloride, b.p. 130 - 134 (0.4 mm).

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

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

Procedure: As in Example 1 except using 4-phenyl-2-pentanone instead of benzyl acetone, and iso butyryl chloride instead of benzoyl chloride b.p. 130-134 (0.4 mm).

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

Procedure: Sodium hydride (0.1702 g, 7.09 mmol) was added slowly to a NaCl ice bath containing EtOH (2.6 mL, 2.7 M) stirring under N2. 4-Phenylpentan-2-one (55) (1.0493 g, 6.47 mmol) and diethyloxalate (0.88 mL, 6.47 mmol) were mixed together, and then added to the chilled NaOEt solution. After stirring for 5 minutes, the reaction was warmed to room temperature. After 90 min, the reaction was quenched at 0° C. with 1N HCl and extracted 2× with CH2Cl2. The combined organics were washed with H2O, dried with Na2SO4, filtered, concentrated to provide 56 (0.7230 g, 42.6%) which was used without further purification in the next step. 1H (CDCl3, 400 MHz): δ 7.34-7.16 (5H, m), 6.30 (1H, s), 4.33 (2H, q, J=7.0 Hz), 3.39-3.26 (1H, m), 2.82 (1H, dd, J=15.1, 6.8 Hz), 2.72 (1H, dd, J=15.1, 7.8 Hz), 1.36 (3H, t, J=7.0 Hz), 1.32 (3H, d, J=6.8 Hz) ppm. HPLC: 10.934 min. After stirring for 5 minutes the reaction was quenched at 0° C. with 1N HCl extracted 2× with CH2Cl2 The combined organics were washed with H2O dried with Na2SO4 filtered concentrated

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

Procedure: 1.6 M Methyl lithium (22.8 mL, 36.5 mmol) was added over 1 hour to a stirring 0° C. solution of 3-Phenylbutyric acid (1.8298 g, 11.14 mmol) in dry Et2O (56 mL, 0.2 M): The ice bath was removed, and the reaction was allowed to stir at room temperature for 2⅔ additional hours. Another 0.8 mL MeLi (1.12 mmol, 0.10 equiv) was added, and the reaction was stirred for another 30 minutes. The reaction was then poured into rapidly stirring ice water containing aq. HCl. The organic layer was removed, washed with NaHCO3 and brine, then dried with Na2SO4, filtered and concentrated to achieve pure 55 (1.2324 g, 68.2%): 1H (CDCl3, 400 MHz): δ 7.30 (2H, t, J=7.3 Hz), 7.22 (2H, d, J=7.3 Hz), 7.20 (2H, t, J=7.3 Hz), 3.37-3.27 (1H, m), 2.76 (1H, dd, J=16.1, 6.3 Hz), 2.66 (1H, dd, J=16.1, 7.8 Hz), 2.05 (3H, s), 1.28 (3H, d, J=7.3 Hz) ppm. 13C (CDCl3, 100 MHz): δ 208.01, 146.42, 128.80, 127.03, 126.57, 52.16, 35.67, 30.77, 22.28 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 30.77, 22.28; CH2 carbons: 52.16; CH carbons: 128.80, 127.03, 126.57, 35.67 ppm. HPLC: 10.017 min. (Note: SM has HPLC retention time of 9.041 min.) The ice bath was removed the reaction was stirred for another 30 minutes The organic layer was removed washed with NaHCO3 and brine dried with Na2SO4 filtered concentrated 10.017 min. (Note: SM has HPLC retention time of 9.041 min.)

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

Procedure: Sodium hydride (0.1702 g, 7.09 mmol) was added slowly to a NaCl ice bath containing EtOH (2.6 mL, 2.7 M) stirring under N2. 4-Phenylpentan-2-one (55) (1.0493 g, 6.47 mmol) and diethyloxalate (0.88 mL, 6.47 mmol) were mixed together, and then added to the chilled NaOEt solution. After stirring for 5 minutes, the reaction was warmed to room temperature. After 90 min, the reaction was quenched at 0° C. with 1N HCl and extracted 2× with CH2Cl2. The combined organics were washed with H2O, dried with Na2SO4, filtered, concentrated to provide 56 (0.7230 g, 42.6%) which was used without further purification in the next step. 1H (CDCl3, 400 MHz): δ 7.34-7.16 (5H, m), 6.30 (1H, s), 4.33 (2H, q, J=7.0 Hz), 3.39-3.26 (1H, m), 2.82 (1H, dd, J=15.1, 6.8 Hz), 2.72 (1H, dd, J=15.1, 7.8 Hz), 1.36 (3H, t, J=7.0 Hz), 1.32 (3H, d, J=6.8 Hz) ppm. HPLC: 10.934 min. After stirring for 5 minutes the reaction was quenched at 0° C. with 1N HCl extracted 2× with CH2Cl2 The combined organics were washed with H2O dried with Na2SO4 filtered concentrated

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

Procedure: 1.6 M Methyl lithium (22.8 mL, 36.5 mmol) was added over 1 hour to a stirring 0° C. solution of 3-Phenylbutyric acid (1.8298 g, 11.14 mmol) in dry Et2O (56 mL, 0.2 M): The ice bath was removed, and the reaction was allowed to stir at room temperature for 2⅔ additional hours. Another 0.8 mL MeLi (1.12 mmol, 0.10 equiv) was added, and the reaction was stirred for another 30 minutes. The reaction was then poured into rapidly stirring ice water containing aq. HCl. The organic layer was removed, washed with NaHCO3 and brine, then dried with Na2SO4, filtered and concentrated to achieve pure 55 (1.2324 g, 68.2%): 1H (CDCl3, 400 MHz): δ 7.30 (2H, t, J=7.3 Hz), 7.22 (2H, d, J=7.3 Hz), 7.20 (2H, t, J=7.3 Hz), 3.37-3.27 (1H, m), 2.76 (1H, dd, J=16.1, 6.3 Hz), 2.66 (1H, dd, J=16.1, 7.8 Hz), 2.05 (3H, s), 1.28 (3H, d, J=7.3 Hz) ppm. 13C (CDCl3, 100 MHz): δ 208.01, 146.42, 128.80, 127.03, 126.57, 52.16, 35.67, 30.77, 22.28 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 30.77, 22.28; CH2 carbons: 52.16; CH carbons: 128.80, 127.03, 126.57, 35.67 ppm. HPLC: 10.017 min. (Note: SM has HPLC retention time of 9.041 min.) The ice bath was removed the reaction was stirred for another 30 minutes The organic layer was removed washed with NaHCO3 and brine dried with Na2SO4 filtered concentrated 10.017 min. (Note: SM has HPLC retention time of 9.041 min.)

Conditions: temp:22.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 143 mg of CuBr is added to 1.46 g (10 mmol) of cis/trans-benzylideneacetone (3-phenyl-but-3-en-2-one) in 20 ml of absolute dioxane. 9.4 ml (11 mmol) of a 10% solution of trimethyl aluminum in toluene is added to the reaction at room temperature under nitrogen atmosphere and, after completion of the addition, stirred for 10 minutes at 22° C. For hydrolysis of the reaction solution, 1 ml of water dissolved in 5 ml of dioxane is carefully added to the reaction. It is stirred for 10 minutes more and the inorganic precipitate filtered off with dioxane is washed again. The dioxane solution is concentrated by evaporation on a rotary evaporator and the residue is chromatographed on silica gel with ethyl acetate/hexane as eluent. After concentration by evaporation of the fractions, 1.21 g of 4-phenyl-pentan-2-one (75% of theory) is obtained a colorless liquid. after completion of the addition is carefully added to the reaction It is stirred for 10 minutes more the inorganic precipitate filtered off with dioxane is washed again The dioxane solution is concentrated by evaporation on a rotary evaporator the residue is chromatographed on silica gel with ethyl acetate/hexane as eluent After concentration by evaporation of the fractions

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

Procedure: Sodium hydride (0.1702 g, 7.09 mmol) was added slowly to a NaCl ice bath containing EtOH (2.6 mL, 2.7 M) stirring under N2. 4-Phenylpentan-2-one (55) (1.0493 g, 6.47 mmol) and diethyloxalate (0.88 mL, 6.47 mmol) were mixed together, and then added to the chilled NaOEt solution. After stirring for 5 minutes, the reaction was warmed to room temperature. After 90 min, the reaction was quenched at 0° C. with 1N HCl and extracted 2× with CH2Cl2. The combined organics were washed with H2O, dried with Na2SO4, filtered, concentrated to provide 56 (0.7230 g, 42.6%) which was used without further purification in the next step. 1H (CDCl3, 400 MHz): δ 7.34-7.16 (5H, m), 6.30 (1H, s), 4.33 (2H, q, J=7.0 Hz), 3.39-3.26 (1H, m), 2.82 (1H, dd, J=15.1, 6.8 Hz), 2.72 (1H, dd, J=15.1, 7.8 Hz), 1.36 (3H, t, J=7.0 Hz), 1.32 (3H, d, J=6.8 Hz) ppm. HPLC: 10.934 min. After stirring for 5 minutes the reaction was quenched at 0° C. with 1N HCl extracted 2× with CH2Cl2 The combined organics were washed with H2O dried with Na2SO4 filtered concentrated

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

Procedure: 1.6 M Methyl lithium (22.8 mL, 36.5 mmol) was added over 1 hour to a stirring 0° C. solution of 3-Phenylbutyric acid (1.8298 g, 11.14 mmol) in dry Et2O (56 mL, 0.2 M): The ice bath was removed, and the reaction was allowed to stir at room temperature for 2⅔ additional hours. Another 0.8 mL MeLi (1.12 mmol, 0.10 equiv) was added, and the reaction was stirred for another 30 minutes. The reaction was then poured into rapidly stirring ice water containing aq. HCl. The organic layer was removed, washed with NaHCO3 and brine, then dried with Na2SO4, filtered and concentrated to achieve pure 55 (1.2324 g, 68.2%): 1H (CDCl3, 400 MHz): δ 7.30 (2H, t, J=7.3 Hz), 7.22 (2H, d, J=7.3 Hz), 7.20 (2H, t, J=7.3 Hz), 3.37-3.27 (1H, m), 2.76 (1H, dd, J=16.1, 6.3 Hz), 2.66 (1H, dd, J=16.1, 7.8 Hz), 2.05 (3H, s), 1.28 (3H, d, J=7.3 Hz) ppm. 13C (CDCl3, 100 MHz): δ 208.01, 146.42, 128.80, 127.03, 126.57, 52.16, 35.67, 30.77, 22.28 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 30.77, 22.28; CH2 carbons: 52.16; CH carbons: 128.80, 127.03, 126.57, 35.67 ppm. HPLC: 10.017 min. (Note: SM has HPLC retention time of 9.041 min.) The ice bath was removed the reaction was stirred for another 30 minutes The organic layer was removed washed with NaHCO3 and brine dried with Na2SO4 filtered concentrated 10.017 min. (Note: SM has HPLC retention time of 9.041 min.)