Diethyl Carbonate → Ethyl 2-(pyrimidin-4-yl)acetate

HRID 1483982노트

반응식

HRID 1483982 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][N:13]=1.[CH2:18]([O:20][C:21](=O)[O:22]CC)[CH3:19]>>[N:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:21]([O:20][CH2:18][CH3:19])=[O:22])=[N:13][CH:14]=1

참가 물질

4

반응물 3

HCID 7766Diethyl CarbonateHCID 189224-MethylpyrimidineHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 20295406Ethyl 2-(pyrimidin-4-yl)acetate수율 78.1%

반응 조건

온도
-70 °C

실험 절차

To a flask containing LiHMDS (32 mL, 31.89 mmol, 1.0 M in THF) at −70° C., was slowly added 4-methylpyrimidine (1.0 g, 10.63 mmol). After 5 min of stirring at −70° C., diethylcarbonate (1.93 mL, 15.95 mmol) was added, the reaction was slowly warmed to room temperature and stirred for 4 days. The reaction mixture was quenched by addition of 1 N HCl, neutralized with saturated aqueous NaHCO3 and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered, concentrated under reduced pressure and purified by flash chromatography on silica gel (0-100% EtOAc in hexanes) to give the title compound as a yellow oil (1.38 g, 78%). MS 167 (MH+).

후처리

  1. temperaturethe reaction was slowly warmed to room temperature
  2. stirringstirred for 4 days
  3. customThe reaction mixture was quenched by addition of 1 N HCl
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by flash chromatography on silica gel (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-eae529d1e0a94edcb5570689c26028d3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09420814B2

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