m-Chloroperbenzoic acid → Diethyl(benzylsulfinylmethyl)phosphonate

HRID 65981Notes

Reaction equation

HRID 65981 reaction equation
[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>[CH2:1]([S:8]([CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 23420192Diethyl(benzylsulfinylmethyl)phosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 concentated 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.

Workup

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

Sources & evidence

ORD record
ord-5e85e5d5da154898abda42a01b69379b
Source dataset
uspto-grants-1978_12
Patent number
US04129728

Reaction notes

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