ChemicalBook CAS DataBase List (S)-(+)-4-Phenyl-2-oxazolidinone

(S)-(+)-4-Phenyl-2-oxazolidinone synthesis

6synthesis methods

Product Name:(S)-(+)-4-Phenyl-2-oxazolidinone
CAS Number:99395-88-7
Molecular formula:C9H9NO2
Molecular Weight:163.17

2935-35-5 Synthesis

2935-35-5
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105-58-8
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99395-88-7
499 suppliers
$5.00/5g

Yield:99395-88-7 77%

Reaction Conditions:

with potassium carbonate at 130 - 140;

Steps:

4.2.1 Synthesis of (R,S) 4-phenyloxazolidin-2-one 13
General procedure: A dry 250ml three-necked round bottom flask equipped with a thermometer and a 10cm vigreux column with a distillation head, was charged with 4.3g of the (R,S)-phenylglycinol (31.4mmol) obtained and added of 9.3g of diethyl carbonate (79.0mmol) and 0.43g of K₂CO₃ (3.10mmol). The mixture was heated carefully to 130-140°C and the ethanol was distils as it formed. The oily residue was cooled and added by 50ml of CH₂Cl₂ to facilitate the filtration of the remaining potassium carbonate. The organic phase was then washed with a satured solution of NaHCO₃, separated and dried over anhydrous Na₂SO₄, filtrate and evaporated in vacuo. The residue was crystallized from AcOEt/Etp (1:3) to afford 4.3g (26.4mmol, 85%) of 13 as a white solid.

References:

Zampieri, Daniele;Vio, Luciano;Fermeglia, Maurizio;Pricl, Sabrina;Wünsch, Bernhard;Schepmann, Dirk;Romano, Maurizio;Mamolo, Maria Grazia;Laurini, Erik [European Journal of Medicinal Chemistry,2016,vol. 121,p. 712 - 726]