Diethyl dimethylmalonate → HCID 69596330、化合物

HRID 2212569ノート

反応式

HRID 2212569 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 69596330HCID 69596330、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2360fe0e9800427aa0fbc36dea6113d8
出典データセット
uspto-grants-2006_09
特許番号
US07102008B2

反応ノート

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