A rapid synthesis of substituted 4-hydroxymethyl-3-chromene from 2'-hydroxyacetophenone and phenyl vinyl sulfoxide
A two-step synthesis of 6-alkyl-4-hydroxymethyl-3-chromene (6-alkyl-4-hydroxymethyl-2H-1-benzopyran) from addition of phenyl vinyl sulfoxide carbanion to 5'-alkyl-2'-hydroxyacetophenone is described. Application to the synthesis of 4-methyl-3-chromene (4-methyl-2H-1-benzopyran) and 4,4-dimethylchroman (3,4-dihydro-4,4-dimethyl-2H-1-benzopyran) is also presented.
NEW SYNTHESIS OF 4-SUBSTITUTED CHROMANS FROM VINYLIC SULFOXIDES
The condensation of vinylic sulfoxides with substituted o-acetylphenol followed by cyclization afforded in two high yield steps the corresponding 4-hydroxymethyl-2H-chromene, easily transformed into 4,4-dimethyl chroman.
Solladie, Guy,Girardin, Andre
p. 123 - 124
(2007/10/02)
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