Sodium hydride → HCID 178506156, Verbindung

HRID 1601380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1601380
[H-].[Na+].[Cl-].[F:4][C:5]([F:35])([F:34])[C:6]1[CH:33]=[CH:32][C:9](/[CH:10]=[CH:11]/[CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1.[Cl:36][C:37]1[CH:52]=[CH:51][C:40]([CH2:41][S:42][C@H:43]2[CH2:48][CH2:47][C@H:46]([CH:49]=O)[CH2:45][CH2:44]2)=[CH:39][CH:38]=1>CCCCCC.CS(C)=O.C1(C)C=CC=CC=1>[F:35][C:5]([F:4])([F:34])[C:6]1[CH:7]=[CH:8][C:9](/[CH:10]=[CH:11]/[CH:12]=[CH:49]/[C@H:46]2[CH2:45][CH2:44][C@H:43]([S:42][CH2:41][C:40]3[CH:51]=[CH:52][C:37]([Cl:36])=[CH:38][CH:39]=3)[CH2:48][CH2:47]2)=[CH:32][CH:33]=1

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 18367709[(E)-4-(trifluoromethyl)cinnamyl]triphenylphosphonium chlorideHCID 178520994HCID 178520994, Verbindung

Produkt 1

HCID 178506156HCID 178506156, VerbindungAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

After 50 mg (1.14 mmol) of 55% sodium hydride were washed with hexane, it was suspended in 7 ml of dimethyl sulfoxide, followed by stirring of the suspension at 55° C. for 2.5 hours. The mixture was cooled to room temperature and 607 mg (1.26 mmol) of [(E)-4-(trifluoromethyl)cinnamyl]triphenylphosphonium chloride were added thereto. Further, 170 mg (0.63 mmol) of trans-4-[(4-chlorobenzyl)thio]cyclohexanecarboxaldehyde were added to the resulting mixture, followed by stirring of the mixture at room temperature for 15 minutes. The mixture was diluted with toluene and washed with water and an aqueous NaCl solution. After the mixture was dried, the crude product obtained by evaporation of the solvent was subjected to column chromatography using 5 g of silica gel and eluted with a mixed solvent of methylene chloride-hexane (1:2). The eluted portion was recrystallized from hexane to obtain 86 mg (yield: 31%) of the title compound having a melting point of 142 to 144° C.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. stirringby stirring of the mixture at room temperature for 15 minutes
  3. washwashed with water
  4. customAfter the mixture was dried
  5. customthe crude product obtained by evaporation of the solvent
  6. washeluted with a mixed solvent of methylene chloride-hexane (1:2)
  7. customThe eluted portion was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-30523b506ad242578a755a2388fda11b
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977152

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