StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

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

HRID 1436143
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1436143
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86612619tert-butyl(S)-5-(tert-butyldiphenylsilanyloxy)-2-(diethoxyphosphoryl)-4-methylvalerateAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
3×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-1654b09c28da4899893691a459f8fdb1
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07618960B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion