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Lithium acetate → Methyl 2-(quinolin-5-yl)propanoate

HRID 1814305
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1814305
C([O-])(=O)C.[Li+].FC(F)(F)S(O[C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2)(=O)=O.[CH3:24][O:25]/[C:26](/[O:29][Si](C)(C)C)=[CH:27]\[CH3:28]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[N:17]1[C:18]2[C:13](=[C:12]([CH:27]([CH3:28])[C:26]([O:25][CH3:24])=[O:29])[CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:15][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 3474584Lithium acetateHCID 108557751-Methoxy-1-trimethylsilyloxypropeneHCID 114714035-Quinolyl trifluoromethanesulfonate

Produkt 1

HCID 22504014Methyl 2-(quinolin-5-yl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Katalysator
HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of tris(dibenzylideneacetone)-dipalladium (65 mg, 0.14 mmol), 1,1′-bis(diphenylphosphino)ferrocene(155 mg, 0.28 mmol) and lithium acetate(2.8 g, 27.6 mmol) in THF (50 mL) was stirred at room temperature for 5 minutes. To this mixture was added 5-quinolyl trifluoromethanesulfonate and [(E)-1-methoxy-1-propenyl]oxy(trimethyl)silane. The resulting mixture was heated at reflux for 24 hours and then allowed to cool to room temperature. The mixture was filtered, the residue was washed with THF(50 mL) and the solvent was removed under reduced pressure. Following a short silica column and aqueous workup, methyl 2-(5-quinolyl)propanoate was purified by HPLC yield 250 mg, 17%. HPLC (10% to 90% acetonitrile in 0.1N aqueous ammonium acetate over 10 min at 2 mL/min using a Waters Symmetry C18, 150×4.6 mm column) 6.89 min.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 24 hours
  3. filtrationThe mixture was filtered
  4. washthe residue was washed with THF(50 mL)
  5. customthe solvent was removed under reduced pressure
  6. customwas purified by HPLC yield 250 mg, 17%
  7. custom6.89 min.

Quellen und Nachweise

ORD-Eintrag
ord-3c9fd161dd6f4cecb9d05c0c59617e0f
Quelldatensatz
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06875765B2

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