反应详情

To a suspension of sodium hydride (1.31 g, 80% suspension in mineral oil, 43.8 mM) in 65 ml of tetrahydrofuran (THF), cooled in an ice bath, is added dropwise a solution of 4-benzyloxyindole-3-carboxaldehyde (10.2 g, 39.8 mM) in 55 ml of THF. The mixture is stirred in the cooling bath for an additional 30 minutes; N-methyl-N-phenethyl-2-bromoacetamide (15.3 g, 59.7 mM) is then added. The resulting mixture is stirred at room temperature for 18 hours. Ethyl acetate and 50% brine is added and the layers are separated. The organic layer is washed with brine, dried over magnesium sulfate and concentrated in vacuo to give crude product as a beige oil. Purification on preparative HPLC (silica gel column, 20% ethyl acetate in methylene chloride) gives N-methyl-N-phenethyl-2-(4-benzyloxy-3-formylindol-1-yl)acetamide. (m.p. 120°-122° C.)

1. temperaturecooled in an ice bath
2. stirringThe resulting mixture is stirred at room temperature for 18 hours
3. customthe layers are separated
4. washThe organic layer is washed with brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customto give crude product as a beige oil
8. customPurification on preparative HPLC (silica gel column, 20% ethyl acetate in methylene chloride)