Trimethylsilyl cyanide → 2-Cyano-4-(diethylphosphonomethyl)pyridine

HRID 345312Notes

Reaction equation

HRID 345312 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][N+:13]([O-])=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C[Si]([C:21]#[N:22])(C)C>C(N(CC)CC)C>[C:21]([C:14]1[CH:15]=[C:10]([CH2:9][P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=[CH:12][N:13]=1)#[N:22]

Participants

4

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 145414374-(diethylphosphonomethyl)pyridine-N-oxide

Product 1

HCID 145414382-Cyano-4-(diethylphosphonomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1.2 g of 4-(diethylphosphonomethyl)pyridine-N-oxide, 1.35 ml of triethylamine and 2.6 ml of trimethylsilylcyanide is heated at 90° for 1 hour. The volatiles are removed in vacuo and the residue is dissolved in ethyl acetate and washed with a small volume of aqueous sodium bicarbonate. After drying over magnesium sulfate the solvent is removed in vacuo to afford 2-cyano-4-(diethylphosphonomethyl)pyridine as an oil.

Workup

  1. temperatureis heated at 90° for 1 hour
  2. customThe volatiles are removed in vacuo
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed with a small volume of aqueous sodium bicarbonate
  5. dry with materialAfter drying over magnesium sulfate the solvent
  6. customis removed in vacuo

Sources & evidence

ORD record
ord-1e89386adf1941feb5daf4c64ecec371
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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