反应详情

To a cooled (ice bath) solution of bis (dimethylamino)methane (0.34 g) in dichloromethane (25 ml), acetyl chloride was added dropwise over 5 minutes. After stirring for 10 minutes, 5-phenoxyindole (0.51 g) was added and stirring continued for a further one hour at room temperature. The mixture was basified with aqueous 2N sodium hydroxide, brine (50 ml) added and the organic phase separated washed with water (2×50 ml), dried (MgSO4) and the solvent removed at reduced pressure. The residue was dissolved in dimethylformamide (25 ml) and potassium cyanide (0.62 g) and iodomethane (0.61 g) added. After stirring for 48 hours, the mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic phases were washed with water (4×50 ml), dried (MgSO4) and solvent removed at reduced pressure to give 3-cyanomethyl-5-phenoxyindole (0.57 g).

1. additionwas added dropwise over 5 minutes
2. stirringstirring
3. waitcontinued for a further one hour at room temperature
4. additionadded
5. customthe organic phase separated
6. washwashed with water (2×50 ml)
7. dry with materialdried (MgSO4)
8. customthe solvent removed at reduced pressure
9. dissolutionThe residue was dissolved in dimethylformamide (25 ml)
10. additionpotassium cyanide (0.62 g) and iodomethane (0.61 g) added
11. stirringAfter stirring for 48 hours
12. additionthe mixture was diluted with water (50 ml)
13. extractionextracted with ethyl acetate (3×50 ml)
14. washThe combined organic phases were washed with water (4×50 ml)
15. dry with materialdried (MgSO4) and solvent
16. customremoved at reduced pressure