Potassium Carbonate → (4R)-5,5-Dimethyl-4-phenyl-1,3-oxazolidin-2-one

HRID 2392833Notes

Reaction equation

HRID 2392833 reaction equation
[OH:1][C:2]([CH3:18])([CH3:17])[C@H:3]([NH:10][C:11](=[O:16])C(Cl)(Cl)Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:4]1([C@@H:3]2[C:2]([CH3:18])([CH3:17])[O:1][C:11](=[O:16])[NH:10]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67618536HCID 67618536, compound

Product 1

HCID 6950851(4R)-5,5-Dimethyl-4-phenyl-1,3-oxazolidin-2-oneYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (14) (1.655 g, 5.33 mmol) in ethanol (140 ml) was added potassium carbonate (0.369 g. 2.67 mmol) and the solution was refluxed for 30 minutes. After concentration in vacuo, dichloromethane was added and the mixture was washed with saturated aqueous sodium chloride solution. Concentration in vacuo gave crude crystalline solid which was purified by recrystallisation in ethyl acetate/pentane to give the title compound (15) (0.939 g, 92%); mp 149° C.; νmax (CHCl3) 1753 cm-1 ; [α]D25 (c 0.5 in CHCl3)=-77.6; (Found: C, 69.32; H, 7.05; N, 7.38. C11H13NO2 requires C, 69.09; H, 6.85; N, 7.33%); δH (200 MHz; CDCl3) 0.93 (3H, s, C(CH3)2), 1.61 (3H, s, C(CH3)2), 4.66 (1H, s, CHPh), 6.25 (1H, s, NH), 7.25-7.44 (5H, m, ArCH); δC (125 MHz; CDCl3 23.53 (CH3), 28.04 (CH3), 65.93 (CH), 84.63 (C), 126.67 (ArCH), 128.72 (ArCH), 128.93 (ArCH), 137.16 (C), 159.75 (CO) ; m/z (CI+, NH3) 192 (M+ +1).

Workup

  1. temperaturethe solution was refluxed for 30 minutes
  2. concentrationAfter concentration in vacuo, dichloromethane
  3. additionwas added
  4. washthe mixture was washed with saturated aqueous sodium chloride solution
  5. concentrationConcentration in vacuo
  6. customgave crude crystalline solid which
  7. customwas purified by recrystallisation in ethyl acetate/pentane

Sources & evidence

ORD record
ord-6366aaf1f9b04914ab60a33187a60c25
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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