1-(Bromomethyl)-4-methoxynaphthalene → 1-Methoxynaphthalene

HRID 1585360Notes

Reaction equation

HRID 1585360 reaction equation
BrC[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][CH:4]=1>CN(C=O)C>[CH3:14][O:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=[CH:4][CH:5]=1

Participants

3

Reactant 1

HCID 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 TB AF. [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-f46fa7b33dd44de9a5a3fdb4dbd466de
Source dataset
uspto-grants-1999_08
Patent number
US05935976

Reaction notes

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