N,N,N',N'-Tetramethylethylenediamine → HCID 67081945, 화합물

HRID 1984738노트

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HRID 1984738 반응식
C(OC(OCC)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)C.CN(CCN(C)C)C.C([Li])CCC.[CH3:26][C:27]1[C:32]([CH3:33])=[C:31]([C:34]([CH3:36])=[O:35])[CH:30]=[CH:29][CH:28]=1>CC1CCCO1>[CH3:33][C:32]1[C:27]([CH3:26])=[CH:28][CH:29]=[CH:30][C:31]=1[C:34]([C:6]1[NH:5][CH:9]=[CH:8][N:7]=1)([OH:35])[CH3:36]

참가 물질

6

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 165052',3'-DimethylacetophenoneHCID 38495351-(diethoxymethyl)-1H-imidazoleHCID 178418339Butyllithium

생성물 1

HCID 67081945HCID 67081945, 화합물수율 76.1%

시약·촉매·용매 1

HCID 73012-Methyltetrahydrofuran용매

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온도
-40 °C

실험 절차

1-(Diethoxymethyl)imidazole (76.0 g, 446 mmol) and N,N,N,N-tetramethylethylene diamine (67.6 mL, 446 mmol) were dissolved in 2-methyltetrahydrofuran (400 ml) and cooled to −40° C., under nitrogen. n-Butyl lithium (2.5M in hexane, 180 ml, 446 mmol) was added slowly maintaining the reaction temperature at <−25° C. throughout. The reaction mixture was stirred for an hour and allowed to warm to 0° C., after which 2,3-dimethylacetophenone (44.00 g, 297.00 mmol) was added whilst maintaining the reaction temperature at <15° C. throughout. The reaction was stirred at room temperature overnight and then quenched with aqueous hydrochloric acid (2N, 1 l). The mixture was extracted with ethyl acetate (500 ml) and to the aqueous layer was added sodium carbonate. The aqueous layer was further extracted with ethyl acetate (800 ml) and the combined extracts were washed with water (500 ml), dried (MgSO4) and concentrated in vacuo to give the title compound (48.9 g).

후처리

  1. temperaturemaintaining the reaction temperature at <−25° C. throughout
  2. temperatureto warm to 0° C.
  3. temperaturewhilst maintaining the reaction temperature at <15° C. throughout
  4. stirringThe reaction was stirred at room temperature overnight
  5. customquenched with aqueous hydrochloric acid (2N, 1 l)
  6. extractionThe mixture was extracted with ethyl acetate (500 ml) and to the aqueous layer
  7. additionwas added sodium carbonate
  8. extractionThe aqueous layer was further extracted with ethyl acetate (800 ml)
  9. washthe combined extracts were washed with water (500 ml)
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2f9c2716509c448c812bc305cd72771e
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544706B2

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