Tetrabutylammonium Fluoride → 1-Methoxynaphthalene

HRID 2394152Notes

Reaction equation

HRID 2394152 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].BrC[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([O:31][CH3:32])=[CH:23][CH:22]=1>CN(C=O)C>[CH3:32][O:31][C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 127491851-(Bromomethyl)-4-methoxynaphthalene

Product 1

HCID 166681-Methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy with Example 44, the title compound is obtained from 5(S)-(Boc-amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-[(4-methoxy-1-naphthyl)methyl]hexanoyl-(L)-Val-N-(2-methoxyethyl)amide in abs. DMF using TBAF. [The starting compound for preparing the naphthylmethyl substituent, 1-bromomethyl-4-methoxynaphthalene, is obtained from 1-methoxynaphthalene (Fluka, Buchs, Switzerland) by brominating with I2 /Br2 in CHCl3, reacting the resulting bromide by means of a Grignard reaction and working up with CO2 to form the corresponding acid; reaction of the latter with lithium aluminium hydride to form 1-hydroxymethyl-4-methoxynaphthalene (reduction); and reaction of the latter with PBr3, thereby yielding the desired starting material (see Can. J. Chem. 59, 2629 (1981))].

Sources & evidence

ORD record
ord-790f8f51772d4dd285c93d3a8597fe50
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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