delta-Gluconolactone → 1-Naphthalenemethanol

반응식

[CH2:1]([OH:12])[C@H:2]1O[C:6](=O)[C@H:5](O)[C@@H:4](O)[C@@H:3]1O.C([SiH]([CH2:18][CH3:19])CC)C.B(F)(F)F.CCOCC.[F-].[CH2:30]([N+](CCCC)(CCCC)CCCC)[CH2:31][CH2:32]C>>[C:2]1([CH2:1][OH:12])[C:19]2[C:6](=[CH:30][CH:31]=[CH:32][CH:18]=2)[CH:5]=[CH:4][CH:3]=1

참가 물질

반응물 4

HCID 7027delta-Gluconolactone

HCID 8000Boron trifluoride etherate

HCID 12052Triethylsilane

HCID 2724141Tetrabutylammonium Fluoride

생성물 1

HCID 209081-Naphthalenemethanol

실험 절차

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.