Reacción #52539

Ecuación de reacción

methyl [4-(5-hydroxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate

Compound 135

methyl [4-(5-hydroxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate

carbonyldiimidazole

→

title compound

Rendimiento 31.4%

Methyl[4-(5-imidazol-1-yl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate

Rendimiento 31.4%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in Et2O
3. 3
   Lavadowashed with 5% aqueous NaOH, H2O, and saturated aqueous NaCl
4. 4
   Secadobefore being dried (Na2SO4)
5. 5
   Concentraciónconcentrated under reduced pressure

Procedimiento

A solution of methyl [4-(5-hydroxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate (Compound 135, 140.0 mg, 0.40 mmol) and carbonyldiimidazole (136.0 mg, 0.84 mmol) in 5 mL THF was heated to 65° C. for 48 hours. The solution was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in Et2O and washed with 5% aqueous NaOH, H2O, and saturated aqueous NaCl before being dried (Na2SO4) and concentrated under reduced pressure. Column chromatography (5% MeOH—CH2Cl2) afforded 50.0 mg (31%) of the title compound as a colorless solid.

Fuente