Divinyl sulfone → Di(2-benzyl-3-phenyl-isoxazolidin-5-yl)Sulfone

HRID 2248028

Reaktionsgleichung

Reaktionsgleichung von HRID 2248028
[CH:1](=[N+:8]([O-:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([S:19]([CH:22]=[CH2:23])(=[O:21])=[O:20])=[CH2:18]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:18][CH:17]([S:19]([CH:22]2[O:16][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:23]2)(=[O:21])=[O:20])[O:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6496Divinyl sulfoneHCID 305634Benzenemethanamine,N-(phenylmethylene)-, N-oxide

Produkt 1

HCID 19816343Di(2-benzyl-3-phenyl-isoxazolidin-5-yl)SulfoneAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 2.11 g (10 mmol) of N-benzylidenebenzylamine N-oxide and 1.09 g (5 mmol) of divinyl sulfone in 30 ml of toluene under a nitrogen atmosphere is heated at reflux temperature for 8 hours. The solvent is removed under reduced pressure to give 4.1 g of crude product which is then purified by preparative HPLC (Waters Prep 500A, silica gel, 3:1 heptane:ethyl acetate eluent) to give 0.70 g (26% yield) of a yellow amorphous solid.

Aufarbeitung

  1. temperatureat reflux temperature for 8 hours
  2. customThe solvent is removed under reduced pressure
  3. customto give 4.1 g of crude product which
  4. customis then purified by preparative HPLC (Waters Prep 500A, silica gel, 3:1 heptane:ethyl acetate eluent)

Quellen und Nachweise

ORD-Eintrag
ord-d04bbaa73a1f4045942e7c71db57c9f2
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05037867

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