3-Chloropropyl phenyl ether as a 1,3-dilithiopropane source: sequential reaction with carbonyl compounds

✍ Scribed by Francisco Foubelo; Miguel Yus

• Book ID: 104260404
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 193 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02360-0

✦ Synopsis

The reaction of 3-chloropropyl phenyl ether (1) with lithium powder and a catalytic amount of DTBB (2.5% molar) in THF at -78°C followed by successive treatment with a carbonyl compound [El = ButCHO, Me2CO, (CH2)5CO] at -78 to 20°C and, after 1 h at this temperature, a second one [F~ = ButCHO, PhCHO, MeCOPrn, (CH2)5CO] at -78°(2 leads, after hydrolysis with water, to the formation of the corresponding 1,5-diols (2), in which two different electrophilic fragments have been introduced.