ethyl 3-oxo-5-phenylpentanoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 3-oxo-5-phenylpentanoate (64.2 g, 0.29 mole) was heated between 190° and 210° C. under nitrogen with benzyl alcohol (28.9 ml, 0.28 mole) for 6 hours, the ethanol formed being distilled out of the reaction mixture. The resulting pale yellow oil was essentially pure product, slightly contaminated by starting materials, n.m.r. δ(CCl4) 7.23 (5H, s), 7.06 (5H, s), 5.03 (2H, s), 3.23 (2H, s) and 2.73 (4H, s). being distilled out of the reaction mixture

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl acetoacetate (100 ml, 0.79 mole) in dry tetrahydrofuran (400 ml) was added dropwise with stirring under nitrogen to 50% sodium hydride (41.8 g, 0.87 mole) in dry tetrahydrofuran (80 ml) at 0° C. The resulting solution was stirred for 15 minutes at 0° C. before adding dropwise a solution of n-butyllithium in hexane (460 ml, 1.95 M; 0.90 mole). The resulting orange solution was stirred for a further 15 minutes at 0° C. before adding benzyl chloride (135 ml, 1.18 mole) in dry ether (200 ml) and the solution was then allowed to warm to room temperature over 11/4 hours with stirring before quenching reaction by addition of conc HCl acid (100 ml) in water (200 ml) followed by ether (500 ml). The layers were separated and the aqueous further extracted with ether (3×300 ml). The combined organic layers were washed with water until the wash was neutral, dried (anhydrous MgSO4) and then concentrated. The resulting yellow oil was distilled under vacuum to give a virtually colourless oil (64.2 g, 37%), b.p. 118°-126° C. at 0.7 mmHg, n.m.r. δ(CDCl3) 7.08 (5H, s), 4.07 (2H, q, J=7 Hz), 3.23 (2H, s), 2.80 (4H, s) and 1.23 (3H, t, J=7 Hz). The resulting orange solution was stirred for a further 15 minutes at 0° C. to warm to room temperature over 11/4 hours with stirring before quenching reaction The layers were separated the aqueous further extracted with ether (3×300 ml) The combined organic layers were washed with water until the wash dried (anhydrous MgSO4) concentrated The resulting yellow oil was distilled under vacuum

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-oxo-5-phenyl-pentanoic acid ethyl ester (1.6 g, 7.76 mmol) in methylene chloride (18 mL) is added sulfuryl chloride (1.15 g, 8.53 mmol) dropwise. After stirred at room temperature for 6 hours, the reaction mixture is poured into water, extracted with methylene chloride, is washed water and brine, dried over sodium sulfate. Concentration gave the crude title compound, which is used for the next step without further purification. extracted with methylene chloride is washed water and brine dried over sodium sulfate Concentration

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-oxo-5-phenyl-pentanoic acid ethyl ester (1.6 g, 7.76 mmol) in methylene chloride (18 mL) is added sulfuryl chloride (1.15 g, 8.53 mmol) dropwise. After stirred at room temperature for 6 hours, the reaction mixture is poured into water, extracted with methylene chloride, is washed water and brine, dried over sodium sulfate. Concentration gave the crude title compound, which is used for the next step without further purification. extracted with methylene chloride is washed water and brine dried over sodium sulfate Concentration

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl acetoacetate (2.32 g, 20 mmol) is added to a pre-cold solution of LDA (2.0 M, 20 mL, 40 mmol) in THF (100 mL) at 0° C. After addition, the mixture is stirred for 30 min, then benzyl bromide (3.42 g, 20 mmol) is added dropwise. After stirred at 0° C. for 30 min, the reaction is quenched by 5 N HCl, extracted with ethyl ether. The combined organic layers are washed with water and brine until it is neutral. After addition After stirred at 0° C. for 30 min the reaction is quenched by 5 N HCl extracted with ethyl ether The combined organic layers are washed with water and brine until it

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-oxo-5-phenyl-pentanoic acid ethyl ester (1.6 g, 7.76 mmol) in methylene chloride (18 mL) is added sulfuryl chloride (1.15 g, 8.53 mmol) dropwise. After stirred at room temperature for 6 hours, the reaction mixture is poured into water, extracted with methylene chloride, washed wwashed water and brine, dried over sodium sulfate. Concentration gave the crude title compounds, which is used for the next step without further purification. extracted with methylene chloride washed dried over sodium sulfate Concentration