Chlorotrimethylsilane → N-allyl-3-trimethylsilylpropiolic amide

HRID 370311

Reaction equation

C(OCO[CH2:6][CH3:7])C.C([Li])CCC.C([N-]C(C)C)(C)C.[Li+].[CH2:21]([N:24]=[C:25]=[O:26])[CH:22]=[CH2:23].[CH3:27][Si:28](Cl)([CH3:30])[CH3:29]>C(OC)(C)(C)C.C1COCC1>[CH2:21]([NH:24][C:25](=[O:26])[C:7]#[C:6][Si:28]([CH3:30])([CH3:29])[CH3:27])[CH:22]=[CH2:23]

Participants

Conditions

Temperature: 0 °C

Procedure

Preferred solvents include ethereals such as THF, diethoxymethane and t-butylmethyl ether. At about 0° C., a strong base is added dropwise over a period of about 15 minutes. Examples of strong bases are n-butyl lithium and lithium diisopropyl amide. While still maintaining the temperature near 0° C., a solution of allyl isocyanate in solvent is added dropwise over about 15 minutes. This is followed by the dropwise addition of trimethylsilyl chloride. After holding the reaction mixture at about 0 to about 10° C. for about 3 hours, the reaction is quenched with aqueous ammonium chloride and extracted with dichloromethane. The solvent is evaporated to yield the product, N-allyl-3-trimethylsilylpropiolic amide. ##STR8## wherein TMS is trimethylsilyl, the solvents are methylene chloride or DCE (1,2-dichloroethane), and the acid catalysts are aluminum chloride (AlCl3), ferric chloride (FeCl3) or methanesulfonic acid (MeSO3).

Workup

additionAt about 0° C., a strong base is added dropwise over a period of about 15 minutes
customat about 0 to about 10° C.
customfor about 3 hours
customthe reaction is quenched with aqueous ammonium chloride
extractionextracted with dichloromethane
customThe solvent is evaporated

Sources & evidence

ORD record: ord-767ac93444074d5292a52bfc631b232a
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06140511

Linked notes

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