Ethyl Acetate → 3-(2-Oxo-1,3-oxazolidin-3-yl)benzaldehyde

HRID 38306

반응식

HRID 38306 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])=[O:7])(C)(C)[CH3:2].[H-].[Na+].BrCCO.C(OCC)(=O)C>CN(C)C=O>[O:7]=[C:6]1[N:8]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[O:13])[CH2:2][CH2:1][O:5]1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 167407363-(BOC-Amino)benzaldehyde

생성물 1

HCID 231318243-(2-Oxo-1,3-oxazolidin-3-yl)benzaldehyde수율 29.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 2.93 g of 3-[N-(t-butoxycarbonyl)amino]benzaldehyde in 20 ml of dimethylformamide was added 0.58 g of sodium hydride (60% oily) under ice-cooling. After stirring at room temperature for 1 hour, a solution of 0.93 ml of 2-bromoethanol in 5 ml of dimethylformamide was added dropwise under ice-cooling. After stirring at room temperature for 14 hours, the mixture was heated to stir at 115° C. for 6 hours. Ethyl acetate was added, and this was washed successively with water and an aqueous saturated sedum chloride solution, dried with anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.75 g of oily 3-(2-oxo-oxazolidin-3-yl)benzaldehyde.

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. stirringAfter stirring at room temperature for 14 hours
  4. temperaturethe mixture was heated
  5. stirringto stir at 115° C. for 6 hours
  6. washthis was washed successively with water
  7. dry with materialan aqueous saturated sedum chloride solution, dried with anhydrous sodium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-66c3dc5457934a1f8fca48a64bde6623
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524729B2

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