Reaction of the 2-(bromodifluoromethyl)benzoxazole with tetrakis(dimethylamino)ethylene (TDAE) in the presence of aldehydes. A convenient synthesis of 2-(difluoromethyl)benzoxazole alcohols

Tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of the 2-(bromodifluoromethyl)benzoxazole 1. The generated 2-(difluoromethyl) benzoxazole anion was trapped with several aldehydes 2 – 9, under mild conditions, to give the corresponding 2-(difluoromethyl)benzoxazole alcoh...

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Bibliographic Details
Published in:Tetrahedron letters 1997-02, Vol.38 (5), p.821-824
Main Authors: Burkholder, Conrad, Dolbier, William R., Médebielle, Maurice
Format: Article
Language:English
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Summary:Tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of the 2-(bromodifluoromethyl)benzoxazole 1. The generated 2-(difluoromethyl) benzoxazole anion was trapped with several aldehydes 2 – 9, under mild conditions, to give the corresponding 2-(difluoromethyl)benzoxazole alcohols 10 – 17, in moderate to good yields. Tetrakis(dimethylamino)ethylene (TDA E) was found to be an effective reductant of the 2-(bromodifluoromethyl)benzoxazole 1. The generated 2-(difluoromethyl)benzoxazole anion was trapped with several aldehydes 2 – 9, under mild conditions, to give the corresponding 2-(difluoromethyl)benzoxazole alcohols 10 – 17, in moderate to good yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(96)02440-9