[40207-59-8] · C4H7LiO · 1-Ethoxyvinyllithium · (MW 78.04)
Physical Data: 13C NMR solution studies in THF have been reported.6
Solubility: sol THF.
Form Supplied in: prepared in situ and used directly.
Preparative Methods: prepared in situ under nitrogen by the reaction of Ethyl Vinyl Ether in anhydrous THF with t-Butyllithium.
Handling, Storage, and Precautions: must be prepared and transferred under inert gas (Ar or N2) to exclude oxygen and moisture.
1-Ethoxyvinyllithium adds to benzaldehyde to yield an allylic alcohol (eq 1) which, upon acid hydrolysis, forms the a-hydroxy methyl ketone.2 Reaction also occurs with ketones (eq 2).7
g-Ethoxy dienones have been synthesized in good yields via the intermediate produced by the reaction of 1-ethoxyvinyllithium with 3-ethoxy-2-cyclohexenones.8
Addition of the reagent to a 2-dialkylaminocyclohexanone has been reported (eq 3).9
The reagent adds to conjugated enones at the carbonyl group (eq 4).10-12
Addition of the reagent to an aldehyde in the total synthesis of nikkomycin B produced the vinyl ether, which was not isolated.13 The reagent can also be used to prepare the corresponding cuprate, which adds 1,4 to enones.14
The reagent adds cleanly to isoquinolinium salts (eq 5) to yield, after acid hydrolysis, the methyl ketone.3
Chlorosilanes react with 1-ethoxyvinyllithium4,15 to yield, after acid hydrolysis, acylsilanes with overall yields of 19-31% (eq 6).4
The reagent adds to conjugated sulfones at the b-carbon in good yields (eq 7).5
John F. Sebastian
Miami University, Oxford, OH, USA