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

HRID 2304579
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2304579
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 5-2) and 1.01 g(5.5 mmol) of tosylmethylisocyanide were dissolved in 10 ml of tetrahydrofuran, and then 555 mg(5.5 mmol) of potassium t-butoxide in tetrahydrofuran(10 ml) was slowly added thereto. The reaction solution was stirred for 30 minutes and 10 ml of water was added to the solution in order to stop the reaction. The solvent was removed under reduced pressure. 20 ml of water was added to the residue, which was then 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 column chromatography(eluent: ethyl acetate/n-hexane=1/3, v/v) to obtain 884 mg(4 mmol, Yield 80%) of the title compound.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b2cc3cd5f0f148ef906e3862401e6b82
Quelldatensatz
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06436960B1

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