A convenient synthesis of 2,2-difluoro enol silyl ethers from chlorodifluoromethyl ketones

✍ Scribed by Masayuki Yamana; Takashi Ishihara; Teiichi Ando

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 258 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81449-5

✦ Synopsis

Various chlorodifluoromethyl ketones can be converted to the corresponding 2,2-difluoro enol silyl ethers in good yields, by the action of zinc dust and chlorotrimethylsilane in dry acetonitrile at 60°C. Since the findings of improved methods for the preparation of enol silyl ethers, 1 it has well been recognized that these derivatives from aldehydes and ketones can serve as useful synthetic intermediates in many organic transformations. 2 In contrast to the data accumulated on fluorine-free enol silyl ethers, however, there exist no reports on the preparation of fluorinated enol silyl ethers or their use in organic synthesis. In view of the remarkable enhancement of the specific physiological activity caused by introducing halogen atom(s) into organic molecules, 3 it is of much interest to prepare such a new class of compounds.

This communication is the first paper that describes a method generally applicable for preparing one of such fluorinated enol silyl ethers, i.e., 2,2--difluoro enol silyl ethers (2).