تفاعل #71593

معادلة التفاعل

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

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is cooled to room temperature
2. 2
   ترشيحfiltered through diatomaceous earth
3. 3
   أخرىto remove the catalyst
4. 4
   أخرىthe filtrate is partitioned between ethyl acetate and water
5. 5
   تجفيفdried over anhydrous magnesium sulphate
6. 6
   ترشيحfiltered
7. 7
   أخرىthe filtrate is evaporated in vacuo
8. 8
   أخرىThe residue is further purified by column chromatography on silica gel
9. 9
   غسيلeluting with a mixture of ethyl acetate and hexane

الإجراء التجريبي

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.

المصدر