m-Chloroperbenzoic acid → Diethyl(benzylsulfinylmethyl)phosphonate

HRID 372821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 372821
[CH2:1]([S:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:23]>C(Cl)Cl>[CH2:12]([O:11][P:10]([CH2:9][S:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:23])(=[O:17])[O:14][CH2:15][CH3:16])[CH3:13]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 12536437Diethyl(benzylthiomethyl)phosphonate

Produkt 1

HCID 23420192Diethyl(benzylsulfinylmethyl)phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of diethyl (benzylthiomethyl)phosphonate (10 g., 0.036 mole) in 75 ml. of methylene chloride was, with ice-bath cooling, treated with 7.29 g. (0.036 mole) of m-chloroperoxybenzoic acid portionwise. After the addition was complete, the mixture was stirred for 1 hour at ambient temperature, filtered to remove precipitate, and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel by eluting the column with ethyl acetate which gave 5.9 g. of the title compound.

Aufarbeitung

  1. temperaturecooling
  2. additiontreated with 7.29 g
  3. additionAfter the addition
  4. filtrationfiltered
  5. customto remove precipitate
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washby eluting the column with ethyl acetate which
  9. customgave 5.9 g

Quellen und Nachweise

ORD-Eintrag
ord-48b7b2d6cb9942ddb456fbc435822287
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04092349

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