1-(Trimethylsilyl)pyrrolidin-2-one → HCID 67883823, Verbindung

HRID 1613596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613596
[O:1]1[CH:8]2[CH:2]1[CH2:3][CH2:4][O:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=12.C[Si](C)(C)[N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[O:20]=[C:16]1[CH2:17][CH2:18][CH2:19][N:15]1[C@@H:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH2:3][C@H:2]1[OH:1]

Komponenten

5

Edukt 3

HCID 844611-(Trimethylsilyl)pyrrolidin-2-oneHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 13149080HCID 13149080, Verbindung

Produkt 1

HCID 67883823HCID 67883823, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3.24 g (20 mmol) of 4,5-epoxy-2,3,4,5-tetrahydro-1-benzoxepin and 9.60 g (61 mmol) of N-trimethylsilyl-2-oxo-pyrrolidine are dissolved in 8 ml of dry THF and, while cooling, 6.31 g (20 mmol) of tetrabutylammonium fluoride trihydrate are added in one portion, and the mixture is heated at 100° C. for several hours (TLC check). The mixture is hydrolyzed with ice-water and extracted several times with diethyl ether. The combined diethyl ether extracts are washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration and evaporation of the solvent in vacuo, the residue is crystallized in diisopropyl ether/ethyl acetate. Crystals of melting point 151°-153° C. are obtained.

Aufarbeitung

  1. temperaturewhile cooling
  2. extractionextracted several times with diethyl ether
  3. washThe combined diethyl ether extracts are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and evaporation of the solvent in vacuo
  6. customthe residue is crystallized in diisopropyl ether/ethyl acetate
  7. customCrystals of melting point 151°-153° C. are obtained

Quellen und Nachweise

ORD-Eintrag
ord-9fa850d5e3aa4b0090d554099ca5bc25
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194442

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