HCID 19906402, compound → HCID 19906412, compound

Participants

Reaction Steps

A mixture of 10% (w/w) palladium on carbon (0.75 g) and methyl E-4-[7-(2-carboxyprop-1-enyl)naphth-1-ylmethyl]-3-methoxybenzoate (4.38 g), in tetrahydrofuran (100 ml) was hydrogenated under 3.7 bar of hydrogen for 2 h. To the reaction mixture was added a slurry of 10% (w/w) palladium on carbon (0.75 g) and tetrahydrofuran (20 ml). After hydrogenating for 2 h more, the reaction mixture was filtered through diatomaceous earth with tetrahydrofuran washes. The solvent was evaporated and the residue was dissolved in ether. Evaporation and vacuum drying overnight afforded methyl 4-[7-(2-carboxypropyl)naphth-1-ylmethyl]-3-methoxybenzoate (4.22 g, 96%) as a colorless glassy solid; mp 110.0°-129.0° C.; MS(CI), m/e=393(M+H).

Provenance & Evidence