反应详情

To a solution of N-methoxycarbonyl-O-methyl-L-tyrosine (0.5 g) in dichloromethane (2 ml) was added thionyl chloride (0.29 ml). After stirring for 1 hour at ambient temperature, the reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane (5 ml) and treated with 0.9M ethylaluminum dichloride in dichloromethane (4.4 ml) in an ice-bath. The mixture was allowed to warm to ambient temperature and stirred overnight. The mixture was poured into concentrated hydrochloric acid containing crashed ice and extracted once with dichloromethane. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Purification of the residue by column chromatography on silica gel (eluent; 10:1 dichloromethane-ethyl acetate) gave 6-methoxy-2-(methoxycarbonylamino)indan-1-one (0.12 g).

1. concentrationthe reaction mixture was concentrated in vacuo
2. dissolutionThe residue was dissolved in dichloromethane (5 ml)
3. additiontreated with 0.9M ethylaluminum dichloride in dichloromethane (4.4 ml) in an ice-bath
4. temperatureto warm to ambient temperature
5. stirringstirred overnight
6. additionThe mixture was poured into concentrated hydrochloric acid containing
7. extractionextracted once with dichloromethane
8. washThe extract was washed with water and brine
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated in vacuo
11. customPurification of the residue by column chromatography on silica gel (eluent; 10:1 dichloromethane-ethyl acetate)