반응 #54959

반응 방정식

Ethyl-2-[2-(1,1-dimethylethyl)-4-oxo-4H-1-benzopyran-6-yl]propionate

Jones reagent

→

title compound

Ethyl-2-[2,3-dihydro-2-(1,1-dimethylethyl)-4-oxo-4H-1-benzopyran-6-yl]propionate

용매

acetone

ethanol

반응 조건

후처리

1. 1
   기타for a total of 48 hours
2. 2
   기타The catalyst was removed by filtration (`Hyflo` supercel) and the ethanol
3. 3
   기타removed in vacuo
4. 4
   기타affording an oil
5. 5
   기타The excess oxidant was destroyed with methanol
6. 6
   workup.DISSOLUTIONthe reaction mixture was dissolved in water (200 ml)
7. 7
   추출extracted with ether
8. 8
   세척The combined ethereal extracts were washed with water, dilute aqueous sodium bicarbonate solution and water
9. 9
   건조dried (MgSO4)
10. 10
    농축concentrated in vacuo

실험 절차

Ethyl-2-[2-(1,1-dimethylethyl)-4-oxo-4H-1-benzopyran-6-yl]propionate (6.61 g) was taken up in dry ethanol (150 ml) and hydrogenated at 85 p.s.i. with 5% palladium on carbon (0.2 g) and 5% palladium on barium sulphate (0.4 g) for a total of 48 hours. The catalyst was removed by filtration (`Hyflo` supercel) and the ethanol removed in vacuo affording an oil. The oil was taken up in acetone (50 ml) and treated with a slight excess of Jones reagent. The excess oxidant was destroyed with methanol and the reaction mixture was dissolved in water (200 ml) and extracted with ether. The combined ethereal extracts were washed with water, dilute aqueous sodium bicarbonate solution and water, dried (MgSO4) and concentrated in vacuo to give the title compound as an oil - 6 g.

출처