Dimethylformamide → 3,4-Dimethyl-7-(2-methyl-1,3,4-oxadiazol-5-yl)-methoxycoumarin

Reaction equation

O[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])=[C:7]([CH3:13])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:18][C:19]1[O:20][C:21](C)=[N:22][N:23]=1.CN(C)[CH:27]=[O:28]>>[CH3:13][C:7]1[C:8](=[O:12])[O:9][C:10]2[C:5]([C:6]=1[CH3:14])=[C:4]([O:28][CH3:27])[CH:3]=[C:2]([C:21]1[O:20][C:19]([CH3:18])=[N:23][N:22]=1)[CH:11]=2

Participants

Reactant 4

HCID 6228Dimethylformamide2×

HCID 24758Sodium hydride

HCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazole

HCID 54129907-hydroxy-3,4-dimethyl-2H-chromen-2-one

Product 1

HCID 197514643,4-Dimethyl-7-(2-methyl-1,3,4-oxadiazol-5-yl)-methoxycoumarin

Procedure

5.0 g of 7-hydroxy-3,4-dimethylcoumarin in 20 ml of diemthylformamide were added dropwise to a suspension of 0.9 g of NaH (80%) in 50 ml of dimethylformamide at room temperature. After 45 minutes, 3.5 g of 2-chloromethyl-5-methyl-1,3,4-oxadiazole, dissolved in 20 ml of dimethylformamide, were added and the mixture was stirred overnight at room temperature. The reaction solution was hydrolyzed with ice water, and the precipitated solid was filtered off under suction and recrystallized from methanol.