Dimethylformamide → 3,4-Dimethyl-7-(4-isopropylphenyl)-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+].[CH:17]([C:20]1[CH:27]=[CH:26][C:23](CCl)=[CH:22][CH:21]=1)([CH3:19])[CH3:18].CN(C)[CH:30]=[O:31]>>[CH3:13][C:7]1[C:8](=[O:12])[O:9][C:10]2[C:5]([C:6]=1[CH3:14])=[C:4]([O:31][CH3:30])[CH:3]=[C:2]([C:23]1[CH:26]=[CH:27][C:20]([CH:17]([CH3:19])[CH3:18])=[CH:21][CH:22]=1)[CH:11]=2

Participants

Reactant 4

HCID 6228Dimethylformamide3×

HCID 24758Sodium hydride

HCID 749164-Isopropylbenzyl chloride

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

Product 1

HCID 159874333,4-Dimethyl-7-(4-isopropylphenyl)-methoxycoumarin

Procedure

5.7 g of 7-hydroxy-3,4-dimethylcoumarin in 25 ml of dimethylformamide were added dropwise to a suspension of 1.05 g of NaH (80%) in 15 ml of dimethylformamide at room temperature. After 45 minutes, 5.05 g of 4-isopropylbenzyl chloride, dissolved in 20 ml of dimethylformamide, were added and the mixture was stirred overnight at room temperature. The reaction mixture was hydrolyzed with ice water, and the precipitated solid was filtered off under suction and recrystallized from methanol.