Reaction #1478

Reaction equation

(±)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

Solvents

benzene

Conditions

Workup

1. 1
   Temperatureunder reflux for 7 days
2. 2
   Filtrationthe solids were filtered out
3. 3
   Extractionthe solution was extracted with ethyl acetate
4. 4
   WashThe combined organic layer was washed with brine
5. 5
   Otherdried over Na2 SO4
6. 6
   OtherThe solvent was removed under reduced pressure
7. 7
   Otherthe crude material was purified by flash chromatography (silicagel, 10% ethyl acetate in hexane)

Procedure

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.

Source