PURPOSE: To prepare homoallyl alcohols, selectively, faster than the conventional process, in high yield, by reacting an allyl iodide compound with a bivalent tin compound and a carbonyl compound in a polar solvent, and hydrolyzing the reaction product.
CONSTITUTION: The allyl iodide compound of formulaI(R1WR3 are H, alkyl or aryl; R4 and R5 are H, lower alkyl or aryl) (e.g. allyl iodide) is used as a raw material, and is made to react with a bivalent tin compound (e.g. stannous halide, stannous carboxylate, etc.) and a carbonyl compound (e.g. benzaldehyde, acetophenone, etc.) in a polar solvent at -50W+200°C, pref. at room temp. W100°C, and then hydrolyzed at 0W100°C to obtain the homoallyl alcohol compound of formula II (R6 and R7 are H, alkyl or aryl). The process gives selectively the homoallyl alcohol compound wherein the γ-position carbon atom of the allyl iodide compound is directly bonded to the carbon atom of the carbonyl compound.
HARADA TAIRA
SHIYOUDA SHINICHIROU
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