Diethyl Carbonate → 3-ethyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester

HRID 12462노트

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HRID 12462 반응식
[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)[CH3:2].[Li]CCCC.CCCCCC.[C:29](=O)([O:33]CC)[O:30][CH2:31][CH3:32]>C1COCC1.O>[CH2:31]([O:30][C:29]([C:7]1[N:3]([CH2:1][CH3:2])[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)=[N:5][CH:6]=1)=[O:33])[CH3:32]

참가 물질

7

반응물 4

HCID 7766Diethyl CarbonateHCID 8058HexaneHCID 572422981-ethyl-2-naphthalen-1-yl-1H-imidazoleHCID 178418339Butyllithium

생성물 1

HCID 686289133-ethyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 1-ethyl-2-naphthalen-1-yl-1H-imidazole (1.11 g, 5 mmol) in anhydrous THF (30 ml) at −78° C. under nitrogen is added a solution of n-BuLi in hexane (1.6 M, 3.44 ml, 5.5 mmol, 1.1 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 hr, followed by the addition of diethyl carbonate (1.77 g, 15 mmol, 3.0 eq.). The resulting solution is stirred at −78° C. for 30 min, warmed to rt slowly, and stirred for an additional 30 min at rt. Water (30 ml) is added to quench the reaction, and THF is evaporated under reduced pressure. The residue is extracted with EtOAc (30 ml×2) and the combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. The crude product is purified through silica gel chromatography (hexanes/EtOAc, from 8:1 to 4:1) to give 3-ethyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester. LCMS 295 (M+1).

후처리

  1. stirringThe resulting solution is stirred at −78° C. for 30 min
  2. temperaturewarmed to rt slowly
  3. stirringstirred for an additional 30 min at rt
  4. customto quench
  5. customthe reaction, and THF
  6. customis evaporated under reduced pressure
  7. extractionThe residue is extracted with EtOAc (30 ml×2)
  8. washthe combined organic layers are washed with water and brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe crude product is purified through silica gel chromatography (hexanes/EtOAc, from 8:1 to 4:1)

출처 및 근거

ORD 기록
ord-2a1bb3c7e7b748988571efc43482488c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728009B1

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