Triethyl phosphite → Diethyl(benzylthiomethyl)phosphonate

HRID 426467Notes

Reaction equation

HRID 426467 reaction equation
Cl[CH2:2][S:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:11]([O:13][P:14]([O:18]CC)[O:15][CH2:16][CH3:17])[CH3:12]>>[CH2:11]([O:13][P:14]([CH2:2][S:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:18])[O:15][CH2:16][CH3:17])[CH3:12]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 319930Benzyl Chloromethyl Sulfide

Product 1

HCID 12536437Diethyl(benzylthiomethyl)phosphonate

Conditions

Temperature
155 °C

Procedure

A mixture of benzyl chloromethyl sulfide (20 g., 0.116 mole), prepared according to the method of Bohme, Fischer and Frank [Ann., 563, 54 (1949)], and triethylphosphite (26.9 g., 0.162 mole) was heated with stirring at 155° C. (bath temperature) for 8 hours under a nitrogen atmosphere. The temperature of the oil bath was then raised to 170° C. and the volatile materials removed by distillation under reduced pressure. The residue was chromatographed on silica by eluting with ethyl acetate/benzene mixtures which gave 21.5 g. of the title compound as a liquid.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureThe temperature of the oil bath was then raised to 170° C.
  4. customthe volatile materials removed by distillation under reduced pressure
  5. customThe residue was chromatographed on silica
  6. washby eluting with ethyl acetate/benzene mixtures which
  7. customgave 21.5 g

Sources & evidence

ORD record
ord-8006e0d8351d4615a46dda7659b2ed0c
Source dataset
uspto-grants-1979_10
Patent number
US04169849

Reaction notes

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