Реакция #52859

Уравнение реакции

chloromethyl methyl ether

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

Compound D5

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

isopropyl ethyl amine

→

title compound

(+/−) Ethyl 4-[(5,5-dimethyl-8-(methoxymethyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl)azo]benzoate

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   ДругоеSolvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   Промывкаthe solution was washed with NaHCO3 (sat.), and brine
4. 4
   СушкаThe organic layer was dried (MgSO4)
5. 5
   ДругоеThe solvent was removed under reduced pressure

Методика

To a solution of (+1-) ethyl 4-[(5,5-dimethyl-8-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)azo]benzoate (Compound D5, 49.7 mg, 0.141 mmol) in 4 ml of dry CH2Cl2 at 0° C. was added isopropyl ethyl amine (0.152 ml, 0.847 mmol) followed by chloromethyl methyl ether (0.0323 ml, 0.423 mmol). The reaction mixture was stirred at room temperature for 12 h. Solvent was removed under reduced pressure, the residue was dissolved in ethyl acetate and the solution was washed with NaHCO3 (sat.), and brine. The organic layer was dried (MgSO4). The solvent was removed under reduced pressure, the residue was purfied by flash chromatography (silica, ethyl acetate:hexane, 1:3) to afford the title compound as a red oil.

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