Benzyl Alcohol → HCID 15725027, Verbindung

HRID 846673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846673
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[C:12]([OH:14])=[O:13].N(C(OCC)=O)=NC(OCC)=O.[CH2:34](O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[C:12]([O:14][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:13]

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15724967HCID 15724967, Verbindung

Produkt 1

HCID 15725027HCID 15725027, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution (5 ml) of 2-(1H-indol-2-yl)thio-2-phenylpropionic acid (1.5 g) and diethyl azodicarboxylate (0.96 g) in anhydrous tetrahydrofuran, a solution (5 ml) of benzyl alcohol (0.81 g) and triphenylphoshine (1.44 g) in anhydrous tetrahydrofuran was added dropwise under an argon atmosphere, and the mixture was stirred at room temperature overnight. The solvent was evaporated off under reduced pressure. Benzene was added to the residue, and deposited crystalline matter was filtered and the solvent was evaporated. The residue was purified by silica gel column chromatography (diluting solvent: n-hexane/ethyl acetate=9:1), and was further recrystallized from ethyl acetate/n-hexane to give 1.37 g (yield 71 %) of the product compound as a colorless scale-like crystal. The melting point was 102°-103° C.

Aufarbeitung

  1. customThe solvent was evaporated off under reduced pressure
  2. additionBenzene was added to the residue
  3. filtrationwas filtered
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (diluting solvent: n-hexane/ethyl acetate=9:1)
  6. customwas further recrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d4b11bd418b743d8893744335ad63d8a
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137909

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