Ethanethiol → HCID 59948695, Verbindung

HRID 651041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 651041
[CH2:1]([SH:3])[CH3:2].[H-].[Na+].[CH:6]1([CH2:12][C@H:13]2[CH2:15][O:14]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[NH4+].[Cl-]>CN(C=O)C>[CH:6]1([CH2:12][C@H:13]([OH:14])[CH2:15][S:3][CH2:1][CH3:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

6

Edukt 4

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59949024HCID 59949024, Verbindung

Produkt 1

HCID 59948695HCID 59948695, VerbindungAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Ethanethiol (317 μL, 4.3 mmol) was added to a 60% dispersion in mineral oil NaH (180 mg, 4.5 mmol) slurry in DMF (26 mL) at ambient temperature. After stirring for 15 minutes, the product from Example 15C (300 mg, 2.1 mmol) in DMF (2.0 mL) was added to the reaction vessel. After stirring for 30 minutes, a solution of saturated NH4Cl was added to the mixture followed by extraction with EtOAc (2×). The organics were combined, dried (MgSO4), and concentrated. The residue was chromatographed (silica gel; EtOAc/hexanes 1:20) to provide 347 mg (80%) of the title compound as a light yellow oil.

Aufarbeitung

  1. stirringAfter stirring for 30 minutes
  2. extractionfollowed by extraction with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed (silica gel; EtOAc/hexanes 1:20)

Quellen und Nachweise

ORD-Eintrag
ord-2c4534df552744e6b483ddf708c7c85a
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277871B1

Notizen zur Reaktion

Wird geladen…