Diethyl dimethylmalonate → HCID 69596330, 화합물

HRID 2212569노트

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HRID 2212569 반응식
C([Li])(C)(C)C.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:11]=[CH:10]2.[CH3:25][CH2:26][O:27][C:28]([C:30]([C:33](OCC)=[O:34])([CH3:32])[CH3:31])=[O:29]>C1COCC1>[CH2:26]([O:27][C:28](=[O:29])[C:30]([CH3:32])([CH3:31])[C:33]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:13]=2)[CH:8]=1)=[O:34])[CH3:25]

참가 물질

5

반응물 3

HCID 15382Diethyl dimethylmalonateHCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 69596330HCID 69596330, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

t-Butyl lithium 1.7 M (99.7 mL, 169.5 mmol) was added slowly to a solution of (6-bromo-naphthalen-2-yloxy)-tert-butyl-dimethyl-silane (26.0 g, 77.1 mmol) in THF (400 mL) cooled to −78° C. under a nitrogen atmosphere. The reaction was stirred at −78° C. for 1 h, and then diethyl dimethyl malonate (43.5 g, 231.2 mmol) was added rapidly. The reaction was stirred an additional 0.5 h, warmed to room temperature, and partitioned between water saturated with KH2PO4 and ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated to give 3-[6-(tert-butyl-dimethyl-silanyloxy)-naphthalen-2-yl]-2,2-dimethyl-3-oxo-propionic acid ethyl ester as an oil.

후처리

  1. stirringThe reaction was stirred an additional 0.5 h
  2. temperaturewarmed to room temperature
  3. custompartitioned between water saturated with KH2PO4 and ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2360fe0e9800427aa0fbc36dea6113d8
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07102008B2

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