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

HRID 2098965
ノート
印刷プレビュー

反応式

HRID 2098965 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-49a907eaa4cc4f1ea9d5b4248f92bb8d
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08450522B2

反応ノート

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