Glutaric anhydride → 2'-(4-Carboxybutanoyloxy)-4,4',6'-trimethoxychalcone

HRID 364661

Reaction equation

HRID 364661 reaction equation
[H-].[Na+].O[C:4]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[C:5]=1[C:6](=[O:17])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[C:26]1(=[O:33])[O:32][C:30](=[O:31])[CH2:29][CH2:28][CH2:27]1.[O:34]1CCCC1>>[C:30]([CH2:29][CH2:28][CH2:27][C:26]([O:32][C:4]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[C:5]=1[C:6](=[O:17])[CH:7]=[CH:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)=[O:33])([OH:31])=[O:34]

Participants

5

Reactant 4

HCID 7940Glutaric anhydrideHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 235736Flavokavain A

Product 1

HCID 538104082'-(4-Carboxybutanoyloxy)-4,4',6'-trimethoxychalconeYield 11%

Procedure

Sodium hydride (76 mg of 60% purity) was added with stirring to an ice-cooled solution of 2'-hydroxy-4,4',6'-trimethoxychalcone (500 mg) in 20 ml of tetrahydrofuran. After 10 minutes, a solution of glutaric anhydride (218 mg) in 3 ml of tetrahydrofuran was added. The mixture was stirred at room temperature for 2 hours and evaporated under reduced pressure. The residue was dissolved in 50 ml of ethyl acetate, which was then extracted with 50 ml of 10% aqueous sodium carbonate. The extract was acidified with hydrochloric acid and shaken with 50 ml of chloroform. The chloroform extract was washed with water, dried over Na2SO4 and evaporated under reduced pressure. Crystallization of the residue from benzene gave 75 mg (11% yield) of 2'-(4-carboxybutanoyloxy)-4,4',6'-trimethoxychalcone as pale yellow crystals; m.p. 131°-132° C.

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in 50 ml of ethyl acetate
  3. extractionwhich was then extracted with 50 ml of 10% aqueous sodium carbonate
  4. stirringshaken with 50 ml of chloroform
  5. extractionThe chloroform extract
  6. washwas washed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated under reduced pressure
  9. customCrystallization of the residue from benzene

Sources & evidence

ORD record
ord-ac0b6e7971bd4474a5bbf35d1f975a0f
Source dataset
uspto-grants-1986_08
Patent number
US04605674

Linked notes

Loading…