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

Ethyl bromoacetate → 3-[2-Azido-2-(2-ethoxycarbonylmethoxyethoxy)ethoxy]benzoic acid

HRID 1923447
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1923447
[N:1]([CH:4]([O:16][CH2:17][CH2:18][OH:19])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[N+:2]=[N-:3].[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1COCC1>[N:1]([CH:4]([O:16][CH2:17][CH2:18][O:19][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[N+:2]=[N-:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 597717663-[2-Azido-2-(2-hydroxyethoxy)ethoxy]benzoic acid

Produkt 1

HCID 597717713-[2-Azido-2-(2-ethoxycarbonylmethoxyethoxy)ethoxy]benzoic acidAusbeute 31,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-[2-azido-2-(2-hydroxyethoxy)ethoxy]benzoic acid (0.535 g, 2 mmol) in dry THF (6 ml) was added NaH (60% dispersion, 0.246 g, 6 mmol) at 0° C. After 10 minutes, ethyl 2-bromoacetate (0.488 ml, 4.4 mmol) was added. The reaction was then warmed up to room temperature and stirred for 4 hours. The reaction was quenched by pouring it into ice-cold water (50 ml). The mixture was extracted with DCM (2×50 ml) and the-DCM extracts were discarded. The aqueous layer was then acidified to pH 2 with 1 N HCl, and extracted with DCM (2×50 ml). These DCM extracts were combined, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography (1×20 cm). The title compound, eluted with 2% methanol in DCM, was obtained as an oil (0.223 g, 31.6%). ES-MS, m/z 351.95 (M−1).

Aufarbeitung

  1. customThe reaction was quenched
  2. additionby pouring it into ice-cold water (50 ml)
  3. extractionThe mixture was extracted with DCM (2×50 ml)
  4. extractionextracted with DCM (2×50 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography (1×20 cm)
  8. washThe title compound, eluted with 2% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-1fa7139b42d44eae8f263e46d1bd5ac5
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178360B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion