Journal of Organic Chemistry p. 5419 - 5425 (1992)
Update date:2022-09-26
Topics:
Usami, Takeshi
Shirai, Naohiro
Sato, Yoshiro
3-<(Dimethylamino)methyl>-2-methylene-2,3-dihydrofuran (5o) and 2-<(dimethylamino)methyl>-3-methylene-2,3-dihydrofuran (12o) and their thiophene analogues 5s and 12s were prepared in high yields by fluoride-ion induced desilylation of N,N-dimethyl-N-<(trimethylsilyl)methyl>(2-furylmethyl)ammonium (3o) and -(3-furylmethyl)ammonium iodides (10o) and their thienylmethyl analogues 3s and 10s.Compound 5s or 12s was successfully converted to 3-<(dimethylamino)methyl>(2-thienylmethyl)lithium (23s) or 2-<(dimethylamino)methyl>(3-thienylmethyl)lithium (26s), which reacted with aldehydes to give <(dimethylamino)-methyl>(2-hydroxyalkyl)thiophenes 25s or 27s, respectively.
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(1992)
