Реакция #1478

Уравнение реакции

(±)ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethyl-5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate

Compound D1

(±)ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethyl-5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate

DCC

→

title compounds

Ethyl 4-[(5,5-dimethyl-8-(carbethoxymethyl)-5,6-dihydronaphthalen-2-yl)azo]benzoate

Растворители

benzene

Условия реакции

Обработка

1. 1
   Температураunder reflux for 7 days
2. 2
   Фильтрацияthe solids were filtered out
3. 3
   Экстракцияthe solution was extracted with ethyl acetate
4. 4
   ПромывкаThe combined organic layer was washed with brine
5. 5
   Другоеdried over Na2 SO4
6. 6
   ДругоеThe solvent was removed under reduced pressure
7. 7
   Другоеthe crude material was purified by flash chromatography (silicagel, 10% ethyl acetate in hexane)

Методика

A solution of (±)ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethyl-5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate (Compound D1, 108 mg, 0.25 mmol), DCC (55.9 mg, 0.271 mmol) and CuCl (36.6 mg, 0.37 mmol) in 8 ml of dry benzene was heated under reflux for 7 days. After cooling to room temperature, the solids were filtered out and the solution was extracted with ethyl acetate. The combined organic layer was washed with brine and dried over Na2 SO4. The solvent was removed under reduced pressure, the crude material was purified by flash chromatography (silicagel, 10% ethyl acetate in hexane) to afford the pure title compounds as red oils.

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