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Hydrochloric Acid → 1-(3-(2-(1-Benzothiophene-3-yl)ethoxy)propyl)-3-azetidinol

HRID 597811
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 597811
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][CH:9]=1.FC(F)(F)C(O)=O.[NH:24]1[CH2:27][CH:26]([OH:28])[CH2:25]1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.C(OCC)(=O)C.O>[S:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:24]2[CH2:27][CH:26]([OH:28])[CH2:25]2)=[CH:9]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21990109HCID 21990109, VerbindungHCID 21990122HCID 21990122, Verbindung

Produkt 1

HCID 235455601-(3-(2-(1-Benzothiophene-3-yl)ethoxy)propyl)-3-azetidinolAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

1.00 g of 3-(2-(3-chloropropoxy)ethyl)-1-benzothiophene was dissolved in 5 ml of dimethyl sulfoxide. Thereafter, 1.10 g of 3-azetidinol trifluoroacetate and 1.63 g of potassium carbonate were added to the obtained solution, and the mixture was then stirred at 70° C. for 2 hours. After cooling, water and ethyl acetate were added to the reaction mixture. The pH of the mixture was adjusted to pH 1 by addition of 6 mol/l hydrochloric acid, and a water layer was then separated. Ethyl acetate was added to the water layer, and the pH of the obtained mixture was adjusted to pH 10 by addition of a 2 mol/l aqueous sodium hydroxide solution, followed by separation of an organic layer. The organic layer was successively washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 10:1), so as to obtain 0.55 g of an achromatic oil product, 1-(3-(2-(1-benzothiophene-3-yl)ethoxy)propyl)-3-azetidinol.

Aufarbeitung

  1. temperatureAfter cooling
  2. customa water layer was then separated
  3. additionEthyl acetate was added to the water layer
  4. additionthe pH of the obtained mixture was adjusted to pH 10 by addition of a 2 mol/l aqueous sodium hydroxide solution
  5. customfollowed by separation of an organic layer
  6. washThe organic layer was successively washed with water
  7. dry with materiala saturated saline solution, and then dried over anhydrous magnesium sulfate
  8. distillationThereafter, the solvent was distilled away under a reduced pressure
  9. customThe residue was purified by column chromatography (eluent; chloroform:methanol=30:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-9bb29b7991a64b35871c741ce5ae4bd6
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897594B2

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