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

Methoxymethyl-triphenylphosphonium chloride → 4-(2,5-Dibromo-4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutanal

HRID 1860674
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1860674
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl-].[CH3:12][O:13]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:34][C:35]1[C:40]([O:41][CH3:42])=[C:39]([OH:43])[C:38]([Br:44])=[CH:37][C:36]=1[CH2:45][C:46]([CH3:50])([CH3:49])[CH:47]=O>C1COCC1.Cl>[Br:34][C:35]1[C:40]([O:41][CH3:42])=[C:39]([OH:43])[C:38]([Br:44])=[CH:37][C:36]=1[CH2:45][C:46]([CH3:50])([CH3:49])[CH2:47][CH:12]=[O:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2733832Lithium HexamethyldisilazideHCID 186241923-(2,5-Dibromo-4-hydroxy-3-methoxyphenyl)-2,2-dimethylpropanal

Produkt 1

HCID 186241724-(2,5-Dibromo-4-hydroxy-3-methoxyphenyl)-3,3-dimethylbutanal

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric Acid
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Lithium bis(trimethylsilyl)amide solution (20 ml, 20 mmol, 1M in THF) was added to a mixture methoxy methyl triphenyl phosphonium chloride (6.9 g, 20 mmol) in 25 ml THF dropwise at 0° C. and stirred for 15 min and it was added to a mixture of the product of STEP 3 (2.6 g, 7.1 mmol ) in 15 ml THF dropwise at 0° C. After 5 min, the reaction was quenched with H2O. The product was extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with H2O, brine, dried with Na0.2SO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/3) to give a brown oil in 1.14 g. It was dissolved in 20 ml THF and 20 ml 2N HCl. The reaction was stirred at room temperature for 30 min. THF was evaporated. The product was extracted with ethyl acetate and washed H2O. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with Na2SO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/3) to yield a viscous oil in 0.783 g. NMR spectra of the product were consistent for the proposed structure.

Aufarbeitung

  1. waitAfter 5 min
  2. customthe reaction was quenched with H2O
  3. extractionThe product was extracted with ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with H2O, brine
  6. customdried with Na0.2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/3)
  9. customto give a brown oil in 1.14 g
  10. stirringThe reaction was stirred at room temperature for 30 min
  11. customTHF was evaporated
  12. extractionThe product was extracted with ethyl acetate
  13. washwashed H2O
  14. extractionThe aqueous layer was extracted with ethyl acetate
  15. washThe combined organic layer was washed with brine
  16. dry with materialdried with Na2SO4
  17. concentrationconcentrated
  18. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/3)
  19. customto yield a viscous oil in 0.783 g

Quellen und Nachweise

ORD-Eintrag
ord-93fafea441424428b75c67fd1217f11a
Quelldatensatz
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06531494B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion