Reductive lithiation of 3,5-dimethoxybenzyl methyl ether was successfully performed with lithium wire and a catalytic amount of naphthalene in dry tetrahydrofuran at -15 degreesC, leading to the quantitative generation of 3,5-dimethoxybenzyllithium. This organometallic compound, which can be stored for at least 24 h, was trapped with a variety of different electrophiles, including, besides aldehydes, non-functionalized and functionalized. alkyl halides and an epoxide. Accordingly, it is a useful intermediate in the synthesis of 5-substituted natural and non-natural resorcinols
Practical Generation of 3,5-Dimethoxybenzyllithium: Application to the Synthesis of 5-Substituted-Resorcinols / Azzena, Ugo Gavino; G., Dettori; M. V., Idini; Pisano, Luisa; G., Sechi. - In: APPLIED ORGANOMETALLIC CHEMISTRY. - ISSN 0268-2605. - 17:11(2003), pp. 851-855. [10.1002/aoc.531]
Practical Generation of 3,5-Dimethoxybenzyllithium: Application to the Synthesis of 5-Substituted-Resorcinols
AZZENA, Ugo Gavino;PISANO, Luisa;
2003-01-01
Abstract
Reductive lithiation of 3,5-dimethoxybenzyl methyl ether was successfully performed with lithium wire and a catalytic amount of naphthalene in dry tetrahydrofuran at -15 degreesC, leading to the quantitative generation of 3,5-dimethoxybenzyllithium. This organometallic compound, which can be stored for at least 24 h, was trapped with a variety of different electrophiles, including, besides aldehydes, non-functionalized and functionalized. alkyl halides and an epoxide. Accordingly, it is a useful intermediate in the synthesis of 5-substituted natural and non-natural resorcinolsI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
