Potassium hydride-Hexamethylphosphoric triamide

Related Reagents. A(,A(-Diitiethylformaniide N,N -Dimethylpropyleneurea Dimethyl Sulfoxide Hexam-ethylphosphoric Triamide-Thionyl Chloride Lithium Chloride-Hexamethylphosphoric Triamide l-Methyl-2-pyrrolidinone Potassium t-Butoxide-Hexamethylphosphorie Triamide Potassium Hydride-Hexamethylphosphorie Triamide Potassium Hydroxide-Hexamethylphosphoric Triamide A(,A( -Tetramethylethylenediamine. 

A solution of (12) prepared in hexamethylphosphoric triamide (HPMT, 0.5 ml) from ethyl isocyanoacetate (1.7 mmol) and potassium hydride (1.7 mmol), is added to a mixture of S-methyl-A, iV -diphenylisothiourea (0.19 g, 0.8 mmol) and coppcr(I) chloride (0.03 g, 0.3 mmol) in HMPT (0.2 ml) at 0°C. After stirring at 25°C (4h), the reaction is quenched with aqueous ammonium chloride, and extracted three times with ethyl acetate. The combined organic extracts are dried (MgS04) and evaporated. Column chromatography on silica gel (diethyl ether-ethyl acetate, 1 3) gives (13a) (R, R = Ph) (0.19g, 75%), m.p. 157-159°C. 

ALKYLATION Benzyltriethylammonium chloride. n-Butyl mercaptan. Dialkylcar-bonium fluoroborates. Diethoxycarboni-um fluoroborate. Dimethylcopperhthium. Ethyl vinyl ether. Dimethylformamide dimethyl acetal. Dimethyl sulflde. Dimeth-ylsulfonium methylide. Ethyl chlorofor-mate. Hexamethylphosphoric triamide. Lithium diisopropylamide. Lithium N-iso-propylcydohexylamide. O-Methyldiben-zofuranium fluoroborate. Methyl fluoro-sulfonate. Naththalene-Sodium. Palladi-um(II) chloride. 1,2,2,6,6-Pentamethyl-piperidine. Potassium hydroxide. Silver oxide. Sodium bis-2-methoxyethoxyalu-minum hydride. Sodium hydride. Thal-lous ethoxide. 

An unusually fast anionic [1,3] shift is observed on treatment of medium-sized-ring 1-vinyl alcohols with potassium hydride in hexamethylphosphoric triamide, e.g., 57, 61, and... 

Related Reagents. Hexamethylphosphoric Triamide N,N, A, N",(V"-Pentamethyldiethylenetriamine Potassium Hydride-s-Butyllithium-iV,iV,iV, iV -Tetramethylethylenediamine (—)-... 

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