m-Chloroperbenzoic acid → 3-(Diethylphosphonomethyl)-2-cyanopyridine

HRID 345314Notes

Reaction equation

HRID 345314 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].ClC1C=CC=C(C(OO)=O)C=1.C[Si]([C:31]#[N:32])(C)C>>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[C:11]([C:31]#[N:32])=[N:12][CH:13]=[CH:14][CH:15]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:31]#[N:32])=[N:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 82115Trimethylsilyl cyanideHCID 104626053-(Diethoxyphosphorylmethyl)pyridine

Product 2

HCID 542333823-(Diethylphosphonomethyl)-2-cyanopyridineHCID 544899365-(Diethylphosphonomethyl)-2-cyanopyridine

Procedure

Treatment of 3-(diethylphosphonomethyl)pyridine (Biochemistry 19, 3400) with m-chloroperbenzoic acid followed by trimethylsilyl cyanide gives both 3-(diethylphosphonomethyl)-2-cyanopyridine and 5-(diethylphosphonomethyl)-2-cyanopyridine, the starting materials for compounds under a) and b).

Sources & evidence

ORD record
ord-ac012df2c4b64d1180f2043e91bddbdb
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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