Dichlorodimethylsilane → HCID 19097746, compound

HRID 256680Notes

Reaction equation

HRID 256680 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 2-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 CDCl3 /TMS showed a 2H multiplet at 2.3 ppm, a 2H multiplet at 3.1 ppm, a 6.5 H 1:1 doublet at 3.7 ppm, and 4.5 aromatic H as multiplets between 7.1 and 8.6 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-7d61400024934bce8e8b48d7088a1e2d
Source dataset
uspto-grants-1993_11
Patent number
US05258469

Reaction notes

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