Chlorotrimethylsilane → N-allyl-3-trimethylsilylpropiolic amide

HRID 1596699

Reaction equation

[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C(OCOCC)C.C([Li])CCC.C([N-]C(C)C)(C)C.[Li+].[CH2:27]([N:30]=[C:31]=[O:32])[CH:28]=[CH2:29].C[Si](Cl)(C)C>C(OC)(C)(C)C.C1COCC1>[CH2:27]([NH:30][C:31](=[O:32])[C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:28]=[CH2:29]

Participants

Conditions

Temperature: 0 °C

Procedure

The reaction is carried out by dissolving trimethylsilylacetylene in an solvent. 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.

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-a31367e9ef604a1bad0292483a4caf64
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291513B1

Linked notes

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