反应详情

温度

50 °C

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).

1. customresulting
2. customfrom decanting water from a 50% (w/w) slurry in water)
3. temperaturecooled
4. additionethyl acetate was added
5. filtrationthe mixture filtered through diatomaceous earth with ethyl acetate
6. washwash
7. washThe organic layer was washed (1N HCl twice
8. dry with materialbrine), dried (MgSO4)
9. customevaporated
10. customPurification by flash chromatography
11. washeluting with methylene chloride, and trituration with ether