Ethanethiol → HCID 59948695, Verbindung

HRID 1532876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532876
[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 min, the product from Example 1308C (300 mg, 2.1 mmol) in DMF (2.0 mL) was added to the reaction vessel. After stirring for 30 min, 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 afford a light yellow oil (347 mg, 80%). 1H NMR (CDCl3, 300 MHz) δ0.80-1.00 (m, 2H), 1.12-1.32 (m, 7H), 1.39-1.75 (m, 6H), 1.81 (m, 1H), 2.42 (dd, J=9, 14 Hz, 1H), 2.56 (q, J=7.5 Hz, 2H), 2.74 (dd, J=3, 14 Hz, 1H), 3.76 (m, 1H); MS (CI/NH3) m/z: 203 (M+H)+.

Aufarbeitung

  1. stirringAfter stirring for 30 min
  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-9a5010c207964655a3c43f1797929f7e
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06204293B1

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