PURPOSE: A specific aromatic silicon compound is converted into a silicon- stabilized carbanion and it is alkylated to produce the titled compound such as female hormone from steadily available starting materials through a shortened process inexpensively in high yield.
CONSTITUTION: A compound of formulaI[X is H, hydroxyl, methoxy; R is alkyl; R1, R2 are H, methyl; Y is halogen, OSO2R8 (R8 is alkyl) or other eliminable group]such as 2-(trimethylsilymethyl)-5-methoxybenzyldimethylamine is made to react with n-butyllithium to form silicon-stabilized carbanion selectively and the product is made to react with a bromide of formula II. The reaction product is converted into its quaternary salt with methyl iodide and the salt is treated with CsF in an acetonitrile solvent to give the objective compound of formula III.
NAKATSUKA MASASHI
ITOU YOSHIHIKO
