[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2].[C:18](Cl)(=[O:20])[CH3:19]>C(Cl)Cl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:17])[O:5][N:4]=1)[CH3:2]In the alternate procedure, 41.8 grams (0.163 moles) of silver trifluoromethanesulfonate is added portionwise to a solution of 33.5 grams (0.148 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-indole in 450 milliliters of methylene chloride. The resulting suspension is then treated by dropwise addition with 12.8 grams (0.163 moles) of acetyl chloride in 50 milliliters of methylene chloride. The temperature rises to 35° C. during the addition. After the addition is complete the mixture is stirred at room temperature for 4 hours and then filtered. The filtrate is washed with 150 milliliters of of 2N sodium hydroxide, water and 2N sodium hydroxide, then dried over anhydrous magnesium sulfate and finally evaporated in vacuo to yield an oil. The oil is crystallized from ether to give 2-(3-ethyl-5-methyl-4-isoxazolyl)-3-acetyl indole, m.p. 170°-173° C.
Loading…
