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

alpha-Methylene butyrolactone → 3-(Tert-butoxycarbonyl)-2-methyl-6-((2-oxo-2,5-dihydrofuran-3-yl)methyl)benzyl acetate

HRID 132421
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 132421
C(OC(N[C:9]1[C:10]([CH3:21])=[C:11]([C:17](I)=[CH:18][CH:19]=1)[CH2:12][O:13][C:14](=[O:16])[CH3:15])=O)(C)(C)C.[CH2:22]=[C:23]1[CH2:28][CH2:27][O:26][C:24]1=[O:25].[C:29]([O-:32])(=[O:31])C.[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([O:13][CH2:12][C:11]1[C:17]([CH2:22][C:23]2[C:24](=[O:25])[O:26][CH2:27][CH:28]=2)=[CH:18][CH:19]=[C:9]([C:29]([O:32][C:10]([CH3:21])([CH3:11])[CH3:9])=[O:31])[C:10]=1[CH3:21])(=[O:16])[CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 68352alpha-Methylene butyrolactoneHCID 517044Potassium AcetateHCID 534147073-(Tert-butoxycarbonylamino)-6-iodo-2-methylbenzyl acetate

Produkt 1

HCID 673195833-(Tert-butoxycarbonyl)-2-methyl-6-((2-oxo-2,5-dihydrofuran-3-yl)methyl)benzyl acetateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Acetic acid 3-tert-butoxycarbonylamino-6-iodo-2-methyl-benzyl ester (575 mg, 1.4 mmol) was dissolved in N,N-dimethylformamide (2.5 mL). α-Methylene-γ-butyrolactone (190 μL, 2.2 mmol) was added to the mixture followed by potassium acetate (420 mg, 4.3 mmol), and then palladium(II)acetate (16 mg, 0.07 mmol). Reaction mixture was heated at 80° C. for 26 hours. Mixture was cooled to room temperature and partitioned between ethyl acetate and aqueous sodium bicarbonate. Layers were separated. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography afforded the title compound as off-white solid in 54% yield. MS m/e (M−H)−=374.

Aufarbeitung

  1. customReaction mixture
  2. temperatureMixture was cooled to room temperature
  3. custompartitioned between ethyl acetate and aqueous sodium bicarbonate
  4. customLayers were separated
  5. dry with materialOrganic layer was dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-645d43c1a88d4bffbe08fc281a63afad
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07384931B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion