Tetrahedron

Reaction of methyl 2, 3-pentadienoate with bromine. Preparation of 4-bromo-5-methyl-5H-furan-2-one

J Font, A Gracia, P De March

Index: Font, J.; Gracia, A.; March, P. de Tetrahedron, 1990 , vol. 46, # 12 p. 4407 - 4416

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Citation Number: 7

Abstract

Treatment of methyl 2, 3-pentadlenoate, 3, with bromine in carbon tetrachloride affords a complex mixture, whose main products are methyl (E)-and (Z)-3, 4-dlbromo-2-pentenoate, 9 and 10, and 4-bromo-5-methyl-5H-furan-2-one, 4. The mechanism of formation of these and other minor compounds is discussed. Hydrolysis of the crude mixture in the presence of barium hydroxide affords lactone 4 in 30% overall yield.

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