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Synthesis 1986; 1986(5): 375-377
DOI: 10.1055/s-1986-31639
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General Method for an Aldol-Type Reaction of 2-Methylbenzothiazole with Carbonyl Compounds

Hidenori Chikashita* , Seiji Ikegami, Takeshi Okumura, Kazuyoshi Itoh
  • *Department of Applied Chemistry, Faculty of Engineering, Kansai University, Suita, Osaka 564, Japan
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Publication Date:
27 September 2002 (online)

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A general and versatile method for the preparation of a variety of β-hydroxybenzothiazoles (aldol-type adducts) by the reaction of α-lithio-2-methylbenzothiazole with carbonyl compounds was proposed. As an example of the use of α-lithio-2-methylbenzothiazole as a masked enolate, the product obtained by the reaction of this lithium reagent with 5-chloro-2-pentanone could be effectively transformed into the corresponding β-oxyaldehyde [2-methyl-2-(2-oxoethyl)-tetrahydrofuran].