Reacción #74461

Ecuación de reacción

triethylsilane

tetrabutylammonium fluoride

gluconolactone

boron trifluoride etherate

→

1-naphthalenemethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONfollowed by addition of the resulting
2. 2
   Otroproduces

Procedimiento

As in Reaction Scheme 2, lithium-halogen exchange of compound (76), followed by addition of the resulting nascent lithiated aromatic to perbenzylated gluconolactone (2), produces a mixture of the corresponding lactols, which is reduced using triethylsilane and boron trifluoride etherate. Subsequent desilylation using tetrabutylammonium fluoride (TBAF) affords 1-naphthalenemethanol (77) in a reasonable yield for the three steps.

Fuente