Chlorotrimethylsilane → HCID 571883, compound

HRID 256681Notes

Reaction equation

HRID 256681 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2].[CH2:9]([O:11][P:12]([O-:16])[O:13][CH2:14][CH3:15])[CH3:10].C[Si](C)(C)Cl>>[N:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH2:2][P:12](=[O:16])([O:13][CH2:14][CH3:15])[O:11][CH2:9][CH3:10])=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 75024-VinylpyridineHCID 3780918Diethylphosphite

Product 1

HCID 571883HCID 571883, compoundYield 54.7%

Procedure

A dry r. b. flask was loaded with 108 ml of 4-vinylpyridine (1 mole) and 129 ml of diethylphosphite (1 mole) under nitrogen. Dropwise addition of 25 ml of trimethylchlorosilane (0.2 mole) gave exothermic reaction to 53° C. with intermittent ice bath cooling. Once the exotherm subsided the reaction mixture was fitted for vacuum distillation. A possible exotherm was noted during distillation with deposition of solids in the lines. The distillation was shut down, the traps cleaned, and distillation recommenced giving 133 g diethyl 2-(4-pyridyl)ethylphosphonate b0.2 =129°-134° C. as a greenish fluid that turned light yellow on standing. Proton NMR in CDCl3 /TMS showed a 6H absorption at 1.3 ppm, 1.9H quintet at 2.1 ppm, 2H multiplet at 2.9 ppm, 4.2H triplet at 4.1 ppm, 2.1H 1:1 doublet at 7.2 ppm, and a 2.1H singlet at 8.5 ppm.

Workup

  1. customgave exothermic
  2. customreaction to 53° C. with intermittent ice bath
  3. temperaturecooling
  4. customwas fitted for vacuum distillation
  5. distillationA possible exotherm was noted during distillation with deposition of solids in the lines
  6. distillationThe distillation
  7. distillationdistillation

Sources & evidence

ORD record
ord-cd8ec825438f47fc9893bf1342ad62fa
Source dataset
uspto-grants-1993_11
Patent number
US05258469

Reaction notes

Loading…