반응 #75889

반응 방정식

calcium hydroxide

benzoyl chloride

ethyl acetate hexane

2-(4-methoxybenzyl)-5-methyl-2H-pyrazol-3-ol

→

[5-hydroxy-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

용매

dioxan

반응 조건

후처리

1. 1
   온도the mixture heated for a further 2 h
2. 2
   기타The solvent was evaporated under reduced pressure
3. 3
   기타the residue partitioned between dichloromethane/10% citric acid
4. 4
   세척The organic phase was washed with brine
5. 5
   건조dried over anhydrous magnesium sulphate
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타to give yellow oil
9. 9
   기타The oil was purified twice by flash chromatography on silica gel, initially using methanol/dichloromethane (1:49)
10. 10
    기타to give a red solid

실험 절차

A solution containing 1.0 g of 2-(4-methoxybenzyl)-5-methyl-2H-pyrazol-3-ol in 30 ml of dioxan was treated with 679 mg of calcium hydroxide and 800 μl of benzoyl chloride, then heated at 110° C. for 2 h. To the mixture was added 20 drops of water and the mixture heated for a further 2 h. The solvent was evaporated under reduced pressure and the residue partitioned between dichloromethane/10% citric acid. The organic phase was washed with brine, then dried over anhydrous magnesium sulphate, filtered and evaporated to give yellow oil. The oil was purified twice by flash chromatography on silica gel, initially using methanol/dichloromethane (1:49) to give a red solid, then ethyl acetate/hexane (1:1 to 2:1) for the elutions to give 400 mg of [5-hydroxy-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone as a yellow gum. Mass spectrum (ES) m/z 323 [M+H]+.

출처