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

Add time:07/19/2019    Source:sciencedirect.com

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 [E1 = ButCHO, Me2CO, (CH2)5CO] at −78 to 20°C and, after 1 h at this temperature, a second one [E2 = ButCHO, PhCHO, MeCOPrn, (CH2)5CO] at −78°C leads, after hydrolysis with water, to the formation of the corresponding 1,5-diols (2), in which two different electrophilic fragments have been introduced.

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