Ethyl propoxyacetate → 3-hydroxy-2-propoxy-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-5-yl]-propionic acid ethyl ester

HRID 2181189ノート

反応式

HRID 2181189 の反応式
[Li].C([N-]C(C)C)(C)C.[CH2:9]([O:11][C:12](=[O:18])[CH2:13][O:14][CH2:15][CH2:16][CH3:17])[CH3:10].[CH3:19][Si:20]([CH3:37])([CH3:36])[CH2:21][CH2:22][O:23][CH2:24][N:25]1[C:33]2[C:28](=[CH:29][C:30]([CH:34]=[O:35])=[CH:31][CH:32]=2)[CH:27]=[CH:26]1>O1CCCC1>[CH2:9]([O:11][C:12](=[O:18])[CH:13]([O:14][CH2:15][CH2:16][CH3:17])[CH:34]([OH:35])[C:30]1[CH:29]=[C:28]2[C:33](=[CH:32][CH:31]=1)[N:25]([CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:36])([CH3:19])[CH3:37])[CH:26]=[CH:27]2)[CH3:10]

参加物

5

反応物 3

HCID 21910278Ethyl propoxyacetateHCID 224856951-(2-Trimethylsilylethyl)oxymethylindole-5-carboxaldehydeHCID 86591433Lithium di-isopropylamide

生成物 1

HCID 695629283-hydroxy-2-propoxy-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-5-yl]-propionic acid ethyl ester収率 91.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a solution of 30 mmol lithium-diisopropylamide in 50 ml tetrahydrofuran were added at −78° C. 4.39 g propoxy-acetic acid ethyl ester [Journal of the American Chemical Society (1996), 118(41), 9901-9907] dissolved in 25 ml of tetrahydrofuran; after 30 min. stirring at −78° C., a solution of 3.31 g 1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole-5-carbaldehyde in 30 ml tetrahydrofuran was added and after another 30 min., the reaction mixture was quenched with 25 ml H2O and then warmed up to ambient temperature. It was then extracted with ethyl acetate and the combined organic phases were washed with water, dried over magnesium sulfate and evaporated to give a light brown oil which was purified by chromatography (silicagel, eluent: gradient of n-heptane/EtOAc) to yield 4.65 g 3-hydroxy-2-propoxy-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-5-yl]-propionic acid ethyl ester (mixture of diasteromers) as a yellow oil.

後処理

  1. customthe reaction mixture was quenched with 25 ml H2O
  2. temperaturewarmed up to ambient temperature
  3. extractionIt was then extracted with ethyl acetate
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give a light brown oil which
  8. customwas purified by chromatography (silicagel, eluent: gradient of n-heptane/EtOAc)

出典と根拠

ORDレコード
ord-119009cca78a4641bbdf91fe2e53e5e9
出典データセット
uspto-grants-2005_05
特許番号
US06890947B2

反応ノート

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