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Methyl (trimethylsilyl)acetate → (E)-Methyl 2-(6-(benzyloxy)-2,2-dimethyl-2,3-dihydroinden-1-ylidene)acetate

HRID 2098965
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HRID 2098965 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si](C)(C)[CH2:13][C:14]([O:16][CH3:17])=[O:15].[CH2:20]([O:27][C:28]1[CH:36]=[C:35]2[C:31]([CH2:32][C:33]([CH3:39])([CH3:38])[C:34]2=O)=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.CCOC(C)=O>[CH2:20]([O:27][C:28]1[CH:36]=[C:35]2[C:31]([CH2:32][C:33]([CH3:39])([CH3:38])/[C:34]/2=[CH:13]\[C:14]([O:16][CH3:17])=[O:15])=[CH:30][CH:29]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
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참가 물질

6

반응물 3

HCID 76210Methyl (trimethylsilyl)acetateHCID 2733832Lithium hexamethyldisilazaneHCID 595908826-(Benzyloxy)-2,2-dimethyl-2,3-dihydroinden-1-one

생성물 1

HCID 59590938(E)-Methyl 2-(6-(benzyloxy)-2,2-dimethyl-2,3-dihydroinden-1-ylidene)acetate수율 45%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8857
Ethyl Acetate
용매

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온도
-78 °C

실험 절차

At −78° C., lithium bis(trimethylsilyl)amide (1.0 M in THF) (3.6 mL, 3.6 mmol) was added slowly to a solution of methyl 2-(trimethylsilyl)acetate (0.59 mL, 3.6 mmol) in THF (20 mL). The mixture was maintained at −78° C. for 7 minutes and then 6-(benzyloxy)-2,2-dimethyl-2,3-dihydroinden-1-one (8.3) (0.535 g, 2.0 mmol) was added in one portion. The resulting mixture was stirred at −78° C. and allowed to warm to room temperature overnight. The reaction mixture was then diluted with EtOAc (200 mL), washed with water and brine, and dried over anhydrous sodium sulfate. After removing solvent, the residue was purified by chromatography (silica gel, 1:5 EtOAc/hexane) to give product 8.4 in 45% yield.

후처리

  1. temperatureto warm to room temperature overnight
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removing solvent
  5. customthe residue was purified by chromatography (silica gel, 1:5 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-49a907eaa4cc4f1ea9d5b4248f92bb8d
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08450522B2

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