Malononitrile → Dihydro-2H-pyran-4,4(3H)-dicarbonitrile

HRID 1608134

Reaction equation

HRID 1608134 reaction equation
Cl[CH:2](Cl)[CH2:3][O:4][CH2:5][CH:6](Cl)Cl.[C:10](#[N:14])[CH2:11][C:12]#[N:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:4]1[CH2:5][CH2:6][C:11]([C:10]#[N:14])([C:12]#[N:13])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 623831,1'-Oxybis(2,2-dichloroethane)

Product 1

HCID 14537194Dihydro-2H-pyran-4,4(3H)-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Flowchart I dichloroethyl ether (1) is reacted with malononitrile (2) in the presence of potassium carbonate in acetonitrile at reflux, giving tetrahydro-4H-pyran-4,4-dicarbonitrile (3) which is then reduced with 1N borane in tetrahydrofuran followed by treatment with hydrochloric acid, giving tetrahydro-4H-pyran-4,4-dimethanamine dihydrochloride (4) which is then reacted with a mixture of sodium acetate and potassium tetrachloroplatinate in water, giving the intermediate compound dichloro(tetrahydro-4H-pyran-4,4-dimethanamine-N,N')platinum (5). ##STR9##

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-ceed7ac1368e4664b31ade80bc10b40d
Source dataset
uspto-grants-1989_09
Patent number
US04870070

Linked notes

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