Organolithium reagents from alkyl phenyl ethers

Article abstract of DOI:10.1016/S0040-4039(98)01659-1

The reaction of primary alkyl or vinyl phenyl ethers (1) as well as 2,3- dihydrobenzofuran (3) with an excess of lithium powder and a catalytic amount of DTBB (5 %) in THF at room temperature leads to the corresponding organolithium intermediates, which by treatment with different electrophiles [H₂O, D₂O, Me₃SiCl, Bu(t)CHO, PhCHO, Me₂CO, Et₂CO, (CH₂)₄CO, (CH₂)₅CO, PhCOMe] and final hydrolysis affords the expected products 2 and 4.