Acetic Acid → Methyl 4-[7-formylnaphth-1-ylmethyl]-3-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoate (1.06 g), sodium hypophosphite hydrate (2.25 g), glacial acetic acid (4 ml), pyridine (8 ml) and water (4 ml) was added Raney nickel (330 mg of material resulting from decanting water from a 50% (w/w) slurry in water). The reaction mixture was heated to 50° C. for 1 h and cooled, ethyl acetate was added and the mixture filtered through diatomaceous earth with ethyl acetate wash. The organic layer was washed (1N HCl twice, brine), dried (MgSO4) and evaporated. Purification by flash chromatography, eluting with methylene chloride, and trituration with ether afforded methyl 4-(7-formylnaphth-1-ylmeth-yl)-3-methoxybenzoate (506 mg, 47%) as a colorless solid; mp 103°-4° C., MS(CI), m/e=336(M+H).

Provenance & Evidence