methyl 3-oxo-5-phenylpentanoate

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

Procedure: A mixture of methyl 3-oxo-5-phenylpentanoate (10 g, 48.5 mmol), 2,6-dichlorobenzaldehyde (8.486 g, 48.5 mmol), acetic acid (0.56 ml, 9.7 mmol), and piperidine (0.24 ml, 2.42 mmol) in benzene (100 ml) was refluxed with azeotropic removal of water for 3 h. After cooling down the mixture, the whole was washed with water, NaHCO3 aqueous solution, and brine. The mixture was dried over Na2SO4 and evaporation of the solvent afforded a crude viscous oil, which was used for subsequent reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers. 1H NMR (CDCl3) δ 7.56 and 7.60 (each s, total 1H), 7.20 (m, 8H), 3.59 and 3.83 (each s, total 3H), 3.14-2.83 (m, 4H),. After cooling down the mixture the whole was washed with water, NaHCO3 aqueous solution, and brine The mixture was dried over Na2SO4 and evaporation of the solvent afforded a crude viscous oil, which was used for subsequent reaction without purification 1:1 mixture of E and Z isomers

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

Procedure: A mixture of methyl 3-oxo-5-phenylpentanoate (10 g, 48.5 mmol), 2,6-dichlorobenzaldehyde (8.486 g, 48.5 mmol), acetic acid (0.56 ml, 9.7 mmol), and piperidine (0.24 ml, 2.42 mmol) in benzene (100 ml) was refluxed with azeotropic removal of water for 3 h. After cooled down, the reaction mixture was wash with water, NaHCO3 aqueous solution, and brine, and dried over Na2SO4. Evaporation of the solvent afforded crude viscous oil, which was used for next reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers. After cooled down the reaction mixture was wash with water, NaHCO3 aqueous solution, and brine dried over Na2SO4 Evaporation of the solvent afforded crude viscous oil, which was used for next reaction without purification 1:1 mixture of E and Z isomers

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

Procedure: A mixture of methyl 3-oxo-5-phenylpentanoate (10 g, 48.5 mmol), 2,6-dichlorobenzaldehyde (8.486 g, 48.5 mmol), acetic acid (0.56 ml, 9.7 mmol), and piperidine (0.24 ml, 2.42 mmol) in benzene (100 ml) was refluxed with azeotropic removal of water for 3 h. After cooling down the mixture, the whole was washed with water, NaHCO3 aqueous solution, and brine. The mixture was dried over Na2SO4 and evaporation of the solvent afforded a crude viscous oil, which was used for subsequent reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers. 1H NMR (CDCl3) δ 7.56 and 7.60 (each s, total 1H), 7.20 (m, 8H), 3.59 and 3.83 (each s, total 3H), 3.14-2.83 (m, 4H),. After cooling down the mixture the whole was washed with water, NaHCO3 aqueous solution, and brine The mixture was dried over Na2SO4 and evaporation of the solvent afforded a crude viscous oil, which was used for subsequent reaction without purification 1:1 mixture of E and Z isomers

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

Procedure: A mixture of methyl 3-oxo-5-phenylpentanoate (10 g, 48.5 mmol), 2,6-dichlorobenzaldehyde (8.486 g, 48.5 mmol), acetic acid (0.56 ml, 9.7 mmol), and piperidine (0.24 ml, 2.42 mmol) in benzene (100 ml) was refluxed with azeotropic removal of water for 3 h. After cooled down, the reaction mixture was wash with water, NaHCO3 aqueous solution, and brine, and dried over Na2SO4. Evaporation of the solvent afforded crude viscous oil, which was used for next reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers. After cooled down the reaction mixture was wash with water, NaHCO3 aqueous solution, and brine dried over Na2SO4 Evaporation of the solvent afforded crude viscous oil, which was used for next reaction without purification 1:1 mixture of E and Z isomers

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

Procedure: A mixture of methyl 3-oxo-5-phenylpentanoate (10 g, 48.5 mmol), 2,6-dichlorobenzaldehyde (8.486 g, 48.5 mmol), acetic acid (0.56 ml, 9.7 mmol), and piperidine (0.24 ml, 2.42 mmol) in benzene (100 ml) was refluxed with azeotropic removal of water for 3 h. After cooled down, the reaction mixture was wash with water, NaHCO3 aqueous solution, and brine, and dried over Na2SO4. Evaporation of the solvent afforded crude viscous oil, which was used for next reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers. After cooled down the reaction mixture was wash with water, NaHCO3 aqueous solution, and brine dried over Na2SO4 Evaporation of the solvent afforded crude viscous oil, which was used for next reaction without purification 1:1 mixture of E and Z isomers

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

Procedure: To a stirred solution of (S)-(−)-α,α-diphenyl-2-pyrrolidinemethanol (770 mg, 3 mmol) in dry THF (100 mL) was added 2 M THF solution of borane-dimethylsulfide complex (11 mL, 22 mmol) at rt under N2. After being stirred at rt for 16 h, a solution of 3-Oxo-5-phenyl-pentanoic acid methyl ester (JACS, 1974, 1082-1087) (6.5 g, 31.5 mmol) in dry THF (20 mL) was added dropwise at rt over a period of 1 h. The resultant clear solution was stirred at rt for another 30 min and was then cooled to 0° C. in an ice bath. The reaction was quenched by the addition of MeOH (90 mL) and the reaction pot was concentrated under reduced pressure. The residue was taken up with EtOAc (200 mL) and washed successively with H2O (100 mL), citric acid (100 mL), 5% NaHCO3 (100 mL) and brine (100 mL). After being dried over Na2SO4, the solvent was removed to afford an oil. Flush column chromatography purification on silica gel gave 3-Hydroxy-5-phenyl-pentanoic acid methyl ester as an oil (3.3 g, 51%) with 92% e.e. (judged from the corresponding Mosher's ester). 1H NMR (300 MHz, CDCl3) δ1.6-1.9 (m, 2H), 2.4-2.6 (m, 2H), 2.65-2.9 (m, 2H), 3.05 (d, 1H, J=6), 3.7 (s, 3H), 3.95-4.10 (m, 1H), 7.10-7.35 (m, 5H). ESMS calcd (C12H16O3): 208.1; found: 209.1 (M+H)+. The resultant clear solution was stirred at rt for another 30 min was then cooled to 0° C. in an ice bath The reaction was quenched by the addition of MeOH (90 mL) the reaction pot was concentrated under reduced pressure washed successively with H2O (100 mL), citric acid (100 mL), 5% NaHCO3 (100 mL) and brine (100 mL) After being dried over Na2SO4 the solvent was removed to afford an oil Flush column chromatography purification on silica gel

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

Procedure: A mixture of methyl 3-oxo-5-phenylpentanoate (10 g, 48.5 mmol), 2,6-dichlorobenzaldehyde (8.486 g, 48.5 mmol), acetic acid (0.56 ml, 9.7 mmol), and piperidine (0.24 ml, 2.42 mmol) in benzene (100 ml) was refluxed with azeotropic removal of water for 3 h. After cooling down the mixture, the whole was washed with water, NaHCO3 aqueous solution, and brine. The mixture was dried over Na2SO4 and evaporation of the solvent afforded a crude viscous oil, which was used for subsequent reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers. 1H NMR (CDCl3) δ 7.56 and 7.60 (each s, total 1H), 7.20 (m, 8H), 3.59 and 3.83 (each s, total 3H), 3.14-2.83 (m, 4H),. After cooling down the mixture the whole was washed with water, NaHCO3 aqueous solution, and brine The mixture was dried over Na2SO4 and evaporation of the solvent afforded a crude viscous oil, which was used for subsequent reaction without purification 1:1 mixture of E and Z isomers

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

Procedure: A mixture of methyl 3-oxo-5-phenylpentanoate (10 g, 48.5 mmol), 2,6-dichlorobenzaldehyde (8.486 g, 48.5 mmol), acetic acid (0.56 ml, 9.7 mmol), and piperidine (0.24 ml, 2.42 mmol) in benzene (100 ml) was refluxed with azeotropic removal of water for 3 h. After cooled down, the reaction mixture was wash with water, NaHCO3 aqueous solution, and brine, and dried over Na2SO4. Evaporation of the solvent afforded crude viscous oil, which was used for next reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers. After cooled down the reaction mixture was wash with water, NaHCO3 aqueous solution, and brine dried over Na2SO4 Evaporation of the solvent afforded crude viscous oil, which was used for next reaction without purification 1:1 mixture of E and Z isomers