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Water → Naphthalen-1-yl(1H-pyrrol-3-yl)methanone

HRID 1059113
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1059113
S([CH2:11][N+:12]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[CH3:14][C:15](C)([O-:17])[CH3:16].[K+].O.C(O[CH2:25][CH3:26])(=O)C.[CH3:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O1C[CH2:36][CH2:35][CH2:34]1>>[C:14]1([C:15]([C:16]2[CH:26]=[CH:25][NH:12][CH:11]=2)=[O:17])[C:36]2[C:30](=[CH:31][CH:32]=[CH:34][CH:35]=2)[CH:29]=[CH:28][CH:27]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 161915Tosylmethyl isocyanideHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 15832251Naphthalen-1-yl(1H-pyrrol-3-yl)methanoneAusbeute 80 %

Versuchsvorschrift

901 mg(5 mmol) of the compound prepared in Preparation 49-2) and 1.01 g(5.5 mmol) of tosylmethylisocyanide were dissolved in 10 ml of tetrahydrofuran. 555 mg(5.5 mmol) of potassium t-butoxide dissolved in 10 ml of tetrahydrofuran was slowly added thereto and the mixture was stirred for 30 minutes. 10 ml of water was added to the reaction solution to stop the reaction and the solvent was removed under reduced pressure. 20 ml of water was added to the residue and the resulting mixture was extracted with ethyl acetate, washed with aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to silica gel column chromatography(eluent: ethyl acetate/hexane=1/3, v/v) to obtain 884 mg(4 mmol, Yield 80%) of the title compound.

Aufarbeitung

  1. additionwas slowly added
  2. customthe reaction
  3. customthe solvent was removed under reduced pressure
  4. addition20 ml of water was added to the residue
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washwashed with aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6f05baa14a5247f0abbf3aab349b463e
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06518429B2

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