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

HRID 2085848Notes

Reaction equation

HRID 2085848 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:11][CH2:10][C:9](O)([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]2[CH:7]=[C:6]([N:19]=[N:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)[CH:5]=[CH:4][C:3]1=2.C1CCC(N=C=NC2CCCCC2)CC1>C1C=CC=CC=1.Cl[Cu]>[CH3:32][C:2]1([CH3:1])[CH2:11][CH:10]=[C:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]2[CH:7]=[C:6]([N:19]=[N:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 22571557(+/-) Ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethy5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate2×

Product 1

HCID 22571504Ethyl 4-[(5,5-dimethyl-8-(carbethoxymethyl)-5,6-dihydronaphthalen-2-yl)azo]benzoate

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 241BenzeneSolvent

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 Na2SO4. The solvent was removed under reduced pressure, the crude material was purified by flash chromatography (silicagel, 10% ethyl acetate in hexane) to afford the pare title compounds as red oils.

Workup

  1. temperatureunder reflux for 7 days
  2. filtrationthe solids were filtered out
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe crude material was purified by flash chromatography (silicagel, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-daa0ee68c7824273b0f40f6ec36c5a01
Source dataset
uspto-grants-2004_04
Patent number
US06720425B2

Reaction notes

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