Sodium hydride → 6-((2R)-2-Hydroxy-4-(3-pyridyl)-1-butoxy)naphthalen-2-yloxyacetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Prepared according to the method described in example 26e) from (2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (1.00 g), 6-Hydroxy-2-naphthyloxyacetic acid methyl ester, sodium hydride (60% dispersion in mineral oil, 0.11 g) in dimethylformamide (15 ml) with heating at 75° C. for 1 hour. The adduct was dissolved in tetrahydrofuran (10 ml) and tetrabutylammonium fluoride hydrate (1.5 g) was added. After 4 hours, the mixture was diluted with water and extracted with ether. The organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with hexane:acetone (3:2 then 1:1) to give the sub-title compound as a solid (0.22 g).

Provenance & Evidence