Dimethylformamide → 3,4-Dimethyl-7-(4-isopropylphenyl)-methoxycoumarin

HRID 2372818Notes

Reaction equation

HRID 2372818 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

5

Reactant 4

HCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 749164-Isopropylbenzyl chlorideHCID 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.

Workup

  1. additionwere added
  2. filtrationthe precipitated solid was filtered off under suction
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-090de1f058b04506b4284efa86225bfe
Source dataset
uspto-grants-1992_03
Patent number
US05100914

Reaction notes

Loading…