| Identification | Back Directory | [Name]
(R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE | [CAS]
160695-26-1 | [Synonyms]
(R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE
R-(+)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE
(R)-4-Phenyl-3-propionyloxazolidin-2-one 95+%
(4R)-4-Phenyl-3-Propionyl-1,3-Oxazolidin-2-One
(4R)-4-phenyl-3-propanoyl-1,3-oxazolidin-2-one
(R)-4-Phenyl-3-propionyl-2-oxazolidinone,99%e.e.
2-Oxazolidinone, 3-(1-oxopropyl)-4-phenyl-, (4R)-
(R)-4-Phenyl-3-propionyl-2-oxazolidinone, ee: 97% | [Molecular Formula]
C12H13NO3 | [MDL Number]
MFCD06658224 | [MOL File]
160695-26-1.mol | [Molecular Weight]
219.24 |
| Chemical Properties | Back Directory | [Melting point ]
83.5-84 °C(Solv: hexane (110-54-3); toluene (108-88-3)) | [Boiling point ]
393.1±31.0 °C(Predicted) | [density ]
1.223±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
-3.13±0.40(Predicted) |
| Hazard Information | Back Directory | [Synthesis]
1. (R)-4-phenyl-2-oxazolidinone (16.3 g, 1.0 eq.) was dissolved in 180 mL of dichloromethane and cooled to 0 °C in an ice bath.
2. Triethylamine (15.2 g, 1.5 eq.) and 4-dimethylaminopyridine (DMAP) (366 mg, 0.03 eq.) were added sequentially with stirring.
3. Propionyl chloride (9.2 g, 1.0 eq.) was added slowly and dropwise, keeping the reaction temperature at 0 °C and continuing to stir for 1 hour.
4. Upon completion of the reaction, the reaction mixture was diluted with methylene chloride and washed sequentially with water and saturated sodium bicarbonate solution.
5. Separate the organic phase and dry with anhydrous sodium sulfate.
6. The solvent was removed by depressurized evaporation to obtain the crude product.
7. The crude product was purified by column chromatography to afford the target compound R-4-phenyl-3-propionyl-2-oxazolidinone (III-a) (20.1 g, 92% yield). | [References]
[1] Organic Letters, 2011, vol. 13, # 21, p. 5762 - 5765
[2] Patent: CN105085322, 2017, B. Location in patent: Paragraph 0065; 0066; 0067; 0068
[3] Organic Process Research and Development, 2005, vol. 9, # 6, p. 827 - 829
[4] Advanced Synthesis and Catalysis, 2018, vol. 360, # 5, p. 965 - 971 |
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