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Ethanethiol → HCID 10298833, Verbindung

HRID 1357677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1357677
C(S)C.[Li]CCCC.Cl.[N:10]1([CH2:16][CH2:17][O:18][C:19]2[CH:45]=[CH:44][C:22]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([O:34]C)=[CH:31][CH:32]=4)[CH:27]=[CH:26][C:25]=3[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=3)=[CH:21][CH:20]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[Li]SCC>CN(C=O)C.CCCCCC.[Li]>[N:10]1([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([OH:34])=[CH:31][CH:32]=4)[CH:27]=[CH:26][C:25]=3[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=3)=[CH:44][CH:45]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6343EthanethiolHCID 98713381-[4-[2-(1-Piperidinyl)-ethoxy]phenoxy]-2-(3-methoxyphenyl)-6-methoxynaphthalene hydrochlorideHCID 178418339ButyllithiumHCID 178506962HCID 178506962, Verbindung

Produkt 1

HCID 10298833HCID 10298833, VerbindungAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittel
HCID 8058HexaneLösungsmittel
HCID 3028194LithiumLösungsmittel

Versuchsvorschrift

A solution of ethanethiol (2.85 ml) in anhydrous DMF (125 mL) under N2 atmosphere was cooled in an ice bath and treated dropwise with 20.1 mL of 1.6 M n-BuLi in hexane. The resulting solution, which was approximately 0.22 M in lithium thioethylate (LiSEt) was allowed to warm to ambient temperature prior to its use. To 1-[4-[2-(1-piperidinyl)-ethoxy]phenoxy]-2-(3-methoxyphenyl)-6-methoxynaphthalene hydrochloride (0.550 g, 1.05 mmol) under nitrogen atmosphere was added 70 mL (15.4 mmol) of the LiSEt solution and the resulting reaction mixture was heated in a 107° C. oil bath for 5 hr. The resulting yellow solution was concentrated under reduced pressure to remove most of the solvent and the yellow oil concentrate was distributed between 300 mL of ethyl acetate and 1N HCl (100 mL) to which 50 g of ice had been added. The ethyl acetate layer extract was washed with 4×25 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated to a foul-smelling yellow oil. The crude material was purified in portions by radial chromatography that employed 5% methanol in chloroform as the elution solvent. The appropriate fractions were combined, concentrated, and dried in vacuo to provide 265 mg (53%) of 1-[4-[2-(1-piperidinyl)ethoxy]-phenoxy]-2-(3-methoxyphenyl)-6-hydroxynaphthalene, as a grey foam.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturewas heated in a 107° C. oil bath for 5 hr
  3. concentrationThe resulting yellow solution was concentrated under reduced pressure
  4. customto remove most of the solvent
  5. concentrationthe yellow oil concentrate
  6. additionhad been added
  7. extractionThe ethyl acetate layer extract
  8. washwas washed with 4×25 mL portions of brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated to a foul-smelling yellow oil
  12. customThe crude material was purified in portions by radial chromatography
  13. concentrationconcentrated
  14. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-050e352360f1448ca8df1ff83f233115
Quelldatensatz
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06593345B1

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