Diisopropyl Ether → HCID 20337244, Verbindung

HRID 2051968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2051968
[CH2:1]([O:8][N:9]([CH2:20][CH2:21]Br)[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:23]([O:30]CC)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26].C(OCC)(=O)C.C(OC(C)C)(C)C>O>[CH2:1]([O:8][N:9]([CH2:20][CH2:21][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 7914Diisopropyl EtherHCID 8857Ethyl AcetateHCID 31215Triethyl phosphiteHCID 20337232HCID 20337232, Verbindung

Produkt 1

HCID 20337244HCID 20337244, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of N-benzyloxy-N-(2-bromoethyl)-p-toluenesulfonamide (16.2 g.) and triethyl phosphite (21.0 g.) was stirred at 160° C. for 10 hours and then cooled to ambient temperature. To the reaction mixture was added ethyl acetate and water. The ethyl acetate layer was separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give an oily residue (20.5 g.). A small volume of isopropyl ether was added to the residue to give crystals, which was separated by filtration and dried to give crystalline diethyl 2-(N-benzyloxy-N-tosylamino)ethylphosphonate (10.6 g.). The object compound (2.1 g.) was also recovered from the mother liquor by subjecting to a column chromatography on silicagel (developing solvent: chloroform)

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. customThe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oily residue (20.5 g.)
  7. customto give crystals, which
  8. customwas separated by filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0719c68507954fe48823f15363f2de45
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04182758

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