ethyl alpha-oxo[1,1'-biphenyl]-4-acetate synthesis

11synthesis methods

Product Name:ethyl alpha-oxo[1,1'-biphenyl]-4-acetate
CAS Number:6244-53-7
Molecular formula:C16H14O3
Molecular Weight:254.28

95-92-1 Synthesis

95-92-1
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ethyl alpha-oxo[1,1'-biphenyl]-4-acetate

6244-53-7
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$252.00/1g

Yield:6244-53-7 55%

Reaction Conditions:

Stage #1: 4-bromo-1,1'-biphenylwith magnesium in tetrahydrofuran at 20; for 0.5 - 0.666667 h;Heating / reflux;
Stage #2: oxalic acid diethyl ester in tetrahydrofuran at -78 - 10; for 1 h;

Steps:

8

To a three-neck round bottom flask containing Mg turnings (1.2 equiv.) equipped with a magnetic stirrer and dimroth condenser was added a solution of alkyl bromide 90 (1 equiv.) in anhydrous THF via syringe and external heating under argon atmosphere. The reaction mixture was refluxed gently for 30-40 min. and then it was cooled to room temperature, before conveying it to a dropping funnel. The Grignard reagent was added dropwise to a solution of diethyl oxalate (1.5 equiv.) in THF at -78°C. The reaction mixture was warmed to 1O⁰C within 1 hour and then was quenched by the addition of saturated ammonium chloride solution. The organic layer was separated, the aqueous layer was extracted with diethyl ether and the combined organic layer was washed with brine, dried over MgSO₄ and evaporated. The residue was purified by flash column chromatography on silica gel (diethyl ether-hexane) to give pure compound 91 in 55-65% yields.Selected data of synthesized α-Keto-esters (91). Ethyl 2-(biphenyl-4-yl)-2-oxoacetate (91.1).¹H NMR (500 MHz, CDCl₃) δ 8.09 (d, J = 8.5 Hz, 2H)₅ 7.74 (d, J = 8.5 Hz₅ 2H)₅ 7.65 (d, J =7.2 Hz₅ 2H)₅ 7.49 (t, J = 7.2 Hz, 2H)₅ 7.43 (t₅ J = 7.2 Hz, IH), 4.47 (q, J = 7.5 Hz, 2H)₅ 1.45(t, J = 7.5 Hz₅ 3H).