Dichlorodimethylsilane → HCID 19097746, compound

HRID 1613911Notes

Reaction equation

HRID 1613911 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].[CH3:9][O:10][P:11]([O-:14])[O:12][CH3:13].Cl[Si](Cl)(C)C>>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:1][CH2:2][P:11](=[O:14])([O:12][CH3:13])[O:10][CH3:9]

Participants

4

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 75212-VinylpyridineHCID 21884954Dimethylphosphite

Product 1

HCID 19097746HCID 19097746, compoundYield 46.5%

Procedure

A dry r. b. flask was loaded with 108 ml of 20 vinylpyridine (1 mole) and 92 ml of dimethylphosphite (1 mole) under nitrogen. Dropwise addition of 25 ml of dichlorodimethylsilane (0.21 mole) gave exothermic reaction to 86° C. even with ice bath cooling. Once the exotherm subsided the reaction mixture was fitted for vacuum distillation. A possible exotherm was noted around 98° C. The distillation was shut down, the traps cleaned, and distillation recommenced giving 100 g dimethyl 2-(2-pyridyl)ethylphosphonate b0.2 =131-146° C. as a yellow fluid. Proton NMR in CDC13 /TMS showed a 2H 1:1 doublet at 3.7 ppm, and 4.5 aromatic H as multiplets between 7.1 and 9.6 ppm.

Workup

  1. customgave exothermic
  2. customreaction to 86° C. even with ice bath
  3. temperaturecooling
  4. customwas fitted for vacuum distillation
  5. customwas noted around 98° C
  6. distillationThe distillation
  7. distillationdistillation

Sources & evidence

ORD record
ord-e95c308977214583a085b2de0d5a8635
Source dataset
uspto-grants-1993_03
Patent number
US05194616

Reaction notes

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