Triphenylphosphine → 1-(2-Chlorophenyl)-3-[1-(1-naphthyl)tetrazol-5-yl]sulfanyl-propan-1-ol

HRID 1988803

Reaktionsgleichung

Reaktionsgleichung von HRID 1988803
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]1([N:25]2[C:29](=[S:30])[N:28]=[N:27][NH:26]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH:38]([OH:42])[CH2:39][CH2:40]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH:38]([OH:42])[CH2:39][CH2:40][S:30][C:29]1[N:25]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[N:26]=[N:27][N:28]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 27317011,2-Dihydro-1-naphthyl-5H-tetrazole-5-thioneHCID 5363146Diisopropyl azodicarboxylateHCID 247774501-(2-chlorophenyl)-1,3-Propanediol

Produkt 1

HCID 52751251-(2-Chlorophenyl)-3-[1-(1-naphthyl)tetrazol-5-yl]sulfanyl-propan-1-olAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

DIAD (82 μL, 0.42 mmol) was added dropwise to a solution of 1,2-dihydro-1-(1-naphthalenyl)-5H-tetrazole-5-thione (80.0 mg, 0.35 mmol), 1-(2-chlorophenyl)-1,3-propanediol (65.4 mg, 0.35 mmol), and PPh3 (110 mg, 0.42 mmol) in THF (10 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h then was concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2:(CH3)2CO, 95:5) to give the title compound (70 mg, 50% yield) as a white solid.

Aufarbeitung

  1. concentrationthen was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (CH2Cl2:(CH3)2CO, 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-8b12d9e956ee4ad8b6655ccab66bd4c6
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642277B2

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