반응 #71593

반응 방정식

1,2-dimethoxyethane

lithium hydroxide monohydrate

2,6-diethyl-4-methylphenylboronic acid

→

2-(2,6-diethyl-4-methylphenyl)-5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione

용매

water

반응 조건

후처리

1. 1
   온도The mixture is cooled to room temperature
2. 2
   여과filtered through diatomaceous earth
3. 3
   기타to remove the catalyst
4. 4
   기타the filtrate is partitioned between ethyl acetate and water
5. 5
   건조dried over anhydrous magnesium sulphate
6. 6
   여과filtered
7. 7
   기타the filtrate is evaporated in vacuo
8. 8
   기타The residue is further purified by column chromatography on silica gel
9. 9
   세척eluting with a mixture of ethyl acetate and hexane

실험 절차

A portion of the ylide (0.70 g, 1.76 mmol) prepared in step 5, 2,6-diethyl-4-methylphenylboronic acid (0.372 g, 1.93 mmol), palladium acetate (0.02 g, 0.09 mmol), tetrabutylammonium bromide (0.583 g, 1.76 mmol) and lithium hydroxide monohydrate (0.222 g, 5.28 mmol) are added to a mixture of 1,2-dimethoxyethane (20 ml) and water (5 ml) and the mixture is heated at 50° C. for 5¾ hours. The mixture is cooled to room temperature, filtered through diatomaceous earth to remove the catalyst, and the filtrate is partitioned between ethyl acetate and water. The organic extracts are combined, dried over anhydrous magnesium sulphate, filtered and the filtrate is evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and hexane to give 2-(2,6-diethyl-4-methylphenyl)-5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione.

출처