반응 #356752

반응 방정식

Ethyl 6-{5′-chloro-2′-[(phenylmethyl)oxy]-2-biphenylyl}-2-pyridinecarboxylate

hydrogen bromide

→

colourless gum

수율 82.3%

Ethyl 6-(5′-chloro-2′-hydroxy-2-biphenylyl)-2-pyridinecarboxylate

수율 82.3%

용매

acetic acid

diethyl ether water

potassium carbonate

acetic acid

반응 조건

후처리

1. 1
   기타The organic phase was separated
2. 2
   건조dried (magnesium sulphate)
3. 3
   기타evaporated
4. 4
   기타chromatographed on silica eluting with ethyl acetate/iso-hexane (1:3)
5. 5
   workup.DISSOLUTIONThe product was dissolved in ethanol (20 ml)
6. 6
   workup.ADDITION60% sodium hydride (2 mg) added
7. 7
   workup.ADDITIONdiluted with water/ether
8. 8
   세척the organic phase washed with saturated sodium bicarbonate solution
9. 9
   건조dried (magnesium sulphate)
10. 10
    기타evaporated
11. 11
    기타chromatographed on silica

실험 절차

Ethyl 6-{5′-chloro-2′-[(phenylmethyl)oxy]-2-biphenylyl}-2-pyridinecarboxylate (1.22 g, 2.75 mmol) was dissolved in acetic acid (5 ml) and 48% hydrogen bromide in acetic acid (5 ml), left at room temperature for 0.5 hours then diluted with diethyl ether/water and basified with potassium carbonate. The organic phase was separated, dried (magnesium sulphate), evaporated and chromatographed on silica eluting with ethyl acetate/iso-hexane (1:3). The product was dissolved in ethanol (20 ml), 60% sodium hydride (2 mg) added and the solution left at room temperature for 16 hours. The resulting solution was acidified with acetic acid, diluted with water/ether and the organic phase washed with saturated sodium bicarbonate solution, dried (magnesium sulphate), evaporated and chromatographed on silica to give 801 mg of colourless gum. LC/MS t=3.33, [MH+] 354.3, 356.3

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