N,N,N',N'-Tetramethylethylenediamine → N,N-diethyl-2-[(chloromethyl)dimethylsilyl]-1-naphthalenecarboxamide

HRID 1604228

반응식

HRID 1604228 반응식
[Li]C(CC)C.C1CCCCC1.CN(CCN(C)C)C.[CH2:20]([N:22]([CH2:35][CH3:36])[C:23]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)=[O:24])[CH3:21].C(=O)=O.CC(C)=O.[Cl:44][CH2:45][Si:46](Cl)([CH3:48])[CH3:47]>C1COCC1.CCOCC>[CH2:35]([N:22]([CH2:20][CH3:21])[C:23]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[Si:46]([CH2:45][Cl:44])([CH3:48])[CH3:47])=[O:24])[CH3:36]

참가 물질

9

반응물 6

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 74393Silane, chloro(chloromethyl)dimethyl-HCID 229388N,N-Diethyl-1-naphthamideHCID 18522661Acetone cardiceHCID 178418400CID 53628100

생성물 1

HCID 15457429N,N-diethyl-2-[(chloromethyl)dimethylsilyl]-1-naphthalenecarboxamide수율 59%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1.3M s-BuLi in cyclohexane (20.3 mL, 26.4 mmol) was added dropwise to an ether/liquid nitrogen-cooled solution of TMEDA (4.0 mL, 26.5 mmol) in THF (15 mL), maintaining the internal reaction temperature <-80° C. To this mixture was added a solution of N,N-diethyl-1-naphthalenecarboxamide (5.0 g, 22.0 mmol) in THF (10 mL), again maintaining the internal reaction temperature <-80° C. The resulting solution was stirred with dry ice/acetone cooling for 30 min, then was recooled to <-80° C. with an ether/liquid nitrogen bath while chloromethyl dimethylsilyl chloride (3.8 mL, 28.8 mmol) was added dropwise. The mixture was warmed to RT to afford a green solution which was diluted with ether and extracted with dilute aq citric acid (2 X), followed with sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and chromatographed with 3:17 ethyl acetate/hexanes to afford 4.3 g of N,N-diethyl-2-[(chloromethyl)dimethylsilyl]-1-naphthalenecarboxamide as a yellow oil, a 59% yield.

후처리

  1. temperaturemaintaining the internal reaction temperature <-80° C
  2. temperatureagain maintaining the internal reaction temperature <-80° C
  3. additionwas added dropwise
  4. customto afford a green solution which
  5. extractionextracted with dilute aq citric acid (2 X)
  6. dry with materialThe ether solution was dried (MgSO4)
  7. concentrationconcentrated
  8. customchromatographed with 3:17 ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-835f14c80df74bd994ba507692370cad
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05994270

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