Benzenesulfonyl chloride → HCID 19838065, Verbindung

HRID 476637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 476637
C([Li])CCC.[CH2:6]([O:8][CH:9]1[NH:13][C:12](=[O:14])[CH:11]=[CH:10]1)[CH3:7].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCCCCC.O1CCCC1>[C:15]1([S:21]([N:13]2[CH:9]([O:8][CH2:6][CH3:7])[CH:10]=[CH:11][C:12]2=[O:14])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 133284325-Ethoxy-1,5-dihydro-2H-pyrrol-2-oneHCID 178418339Butyllithium

Produkt 1

HCID 19838065HCID 19838065, VerbindungAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-35 °C

Versuchsvorschrift

7.37 cm3 of a 1.6M solution of n-butyllithium in n-hexane is added to a solution of 1.5 g of 1,5-dihydro-5-ethoxy-2H-pyrrol-2-one in 40 cm3 of tetrahydrofuran cooled to -35° C., operating at -35°/-30° C. The mixture is agitated for 20 minutes, then cooled to -40° C., and while maintaining the temperature between -38° C. and -40° C., a solution is added of 2.08 g of benzene sulphonyl chloride in 10 cm3 of tetrahydrofuran. The temperature is allowed to return to the ambient, the solvent is evaporated under reduced pressure, and the residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1--1). 1.15 g of the expected product is obtained. m.p. 117°-119° C., crystallized from ethyl ether.

Aufarbeitung

  1. customoperating at -35°
  2. custom-30° C
  3. temperaturecooled to -40° C.
  4. temperaturewhile maintaining the temperature between -38° C. and -40° C.
  5. customthe solvent is evaporated under reduced pressure
  6. customthe residue is chromatographed on silica (eluent: ethyl acetate-n-hexane, 1--1)

Quellen und Nachweise

ORD-Eintrag
ord-f5aad58be9c24afe8e9fc2cca345f486
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04885307

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