Reacción #409090

Ecuación de reacción

Anhydride

cis-1,3-Cyclohexanedicarboxylic Anhydride

triethyl orthoformate

p-Toluenesulfonic acid

→

Diethyl cis-1,3-Cyclohexanedicarboxylate

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto completely consume 1
2. 2
   workup.ADDITIONSolid sodium bicarbonate (0.5 g) was added
3. 3
   Otrothe solvent was removed at reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in toluene (25 mL)
5. 5
   Lavadowashed with saturated aqueous NaHCO3 (5 mL)
6. 6
   Secadodried over Na2SO4
7. 7
   Concentraciónconcentrated
8. 8
   Otroto afford 11.42 g (99%) of cis-2b which

Procedimiento

Anhydride 1 (7.71 g; 50 mmol) was combined with triethyl orthoformate (12.5 mL; 75 mmol; 1.5 equiv) and ethanol (50 mL). p-Toluenesulfonic acid (0.48 g; 2.5 mmol; 0.05 equiv) was added and the reaction mixture was heated overnight at 60° C. to completely consume 1. Solid sodium bicarbonate (0.5 g) was added and the solvent was removed at reduced pressure. The residue was dissolved in toluene (25 mL), washed with saturated aqueous NaHCO3 (5 mL), dried over Na2SO4, and concentrated to afford 11.42 g (99%) of cis-2b which was a single peak by GC analysis.

Fuente