Dimethylcarbamoyl Chloride → Tert-butyl 3-(6-cyano-2-pyridyl)propanoate

HRID 499331노트

반응식

HRID 499331 반응식
[O-][N+:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C[Si]([C:21]#[N:22])(C)C.CN(C)C(Cl)=O.C(OCC)(=O)C>[N+](CC)([O-])=O.O>[C:21]([C:7]1[N:2]=[C:3]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]=[CH:5][CH:6]=1)#[N:22]

참가 물질

7

반응물 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8857Ethyl AcetateHCID 82115Trimethylsilyl cyanideHCID 22939454HCID 22939454, 화합물

생성물 1

HCID 22939301Tert-butyl 3-(6-cyano-2-pyridyl)propanoate수율 82.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6587Nitroethane용매

실험 절차

tert-Butyl 3-(1-oxido-2-pyridyl)propanoate (0.88 g, 3.9 mmol) was dissolved in nitroethane (5 ml). Trimethylsilyl cyanide (0.78 g, 7.9 mmol) and N,N-dimethylcarbamoyl chloride (0.85 g, 7.9 mmol) were added thereto. The reaction mixture was stirred at room temperature for 48 hrs, combined with ethyl acetate and water. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over an hydrous magnesium sulfate. The solvent was evaporated. The residue was subjected to a silica gel (50 g) column chromatography and eluted with hexane-ethyl acetate (3:1, v/v) to give the titled compound (0.75 g, 82%).

후처리

  1. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over an hydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washeluted with hexane-ethyl acetate (3:1

출처 및 근거

ORD 기록
ord-c06e25ed67b74c5c8b6aab832f8d14e8
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767665B2

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