delta-Gluconolactone → 1-Naphthalenemethanol

HRID 46183

Reaction equation

HRID 46183 reaction equation
[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

Participants

5

Reactant 4

HCID 7027delta-GluconolactoneHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 209081-Naphthalenemethanol

Procedure

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.

Workup

  1. additionfollowed by addition of the resulting
  2. customproduces

Sources & evidence

ORD record
ord-bfedbb9e980745f9992a4ed0ae39d433
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Linked notes

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