반응 #3117

반응 방정식

3,4-Dihydroxybenzaldehyde

methyl chlorodifluoroacetate

potassium carbonate

→

title compound

수율 38.0%

4-difluoromethoxy-3-hydroxybenzaldehyde

수율 38.0%

용매

DMF

반응 조건

후처리

1. 1
   기타DMF was removed in vacuo
2. 2
   추출The aqueous layer was extracted three times with ether
3. 3
   세척The combined organic extracts were washed with water, with brine
4. 4
   건조were dried (MgSO4)
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)

실험 절차

3,4-Dihydroxybenzaldehyde (0.50 g, 3.62 mmol, Aldrich), methyl chlorodifluoroacetate (0.52 g, 3.62 mmol, Aldrich) and potassium carbonate (0.50 g, 3.62 mmol) were combined in DMF (5.0 mL) under an argon atmosphere. After stirring at 60°-65° C. for 3 h, DMF was removed in vacuo and the residue was partioned between aqueous 3N HCl and ether. The aqueous layer was extracted three times with ether. The combined organic extracts were washed with water, with brine, were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide the title compound as a white solid (0.20 g, 38%). mp 83°-85° C.

출처