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Sodium hydride → tert-butyl(S)-5-(tert-butyldiphenylsilanyloxy)-2-(diethoxyphosphoryl)-4-methylvalerate

HRID 1436143
ノート
印刷プレビュー

反応式

HRID 1436143 の反応式
[CH2:1]([O:3][P:4]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[H-].[Na+].Br[CH2:20][C@H:21]([CH3:41])[CH2:22][O:23][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[Si:24]([O:23][CH2:22][CH:21]([CH3:41])[CH2:20][C@H:9]([P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])([C:37]([CH3:38])([CH3:39])[CH3:40])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 69007455((R)-3-bromo-2-methylpropoxy)-tert-butyldiphenylsilane

生成物 1

HCID 86612619tert-butyl(S)-5-(tert-butyldiphenylsilanyloxy)-2-(diethoxyphosphoryl)-4-methylvalerate収率 52.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒
3 回

実験手順

A solution tert-butyl diethylphosphonoacetate (64 g) in THF (100 mL) was added dropwise to a suspension of sodium hydride (containing 40% mineral oil, 13.2 g) in THF (400 mL) under ice-cooling, and the reaction mixture was stirred at room temperature for 75 minutes. A solution of ((R)-3-bromo-2-methylpropoxy)-tert-butyldiphenylsilane (99.4 g) in THF (100 mL) was added dropwise to the reaction mixture, which was then heated under reflux for 23 hours. Ice water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 74.6 g of the title compound. The property values of the compound are as follows.

後処理

  1. temperaturecooling
  2. temperaturewas then heated
  3. temperatureunder reflux for 23 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

出典と根拠

ORDレコード
ord-1654b09c28da4899893691a459f8fdb1
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07618960B2

反応ノート

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