Reacción #445548

Ecuación de reacción

dicyclohexylcarbodiimide

4(RS)-tetrahydropyranyloxy-2-(5-carboxypentylthio)-2-cyclopentenone

phenol

pyridine

→

4(RS)-tetrahydropyranyloxy-2-(5-phenoxycarbonylpentylthio)-2-cyclopentenone

Rendimiento 77.5%

Disolventes

dichloromethane

dichloromethane

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   LavadoThe organic layer was washed successively with an aqueous solution of sodium bicarbonate
3. 3
   Secadoan aqueous solution of potassium bisulfate, and an aqueous solution of sodium chloride, dried
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe residue was chromatographed on a silica gel column

Procedimiento

686 mg (2.09 mmoles) of 4(RS)-tetrahydropyranyloxy-2-(5-carboxypentylthio)-2-cyclopentenone and 295 mg (3.14 mmoles) of phenol were dissolved in 10 ml of dichloromethane, and 0.1 ml of pyridine was added. To the solution was added 10 ml of a dichloromethane solution of 860 mg (4.18 mmoles) of dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 18 hours. After the reaction, ethyl acetate was added to the reaction mixture. The organic layer was washed successively with an aqueous solution of sodium bicarbonate, an aqueous solution of potassium bisulfate, and an aqueous solution of sodium chloride, dried, and then concentrated. The residue was chromatographed on a silica gel column using hexane/ethyl acetate (7/2) as an eluent to give 653 mg (1.62 mmoles; yield 77.3%) of 4(RS)-tetrahydropyranyloxy-2-(5-phenoxycarbonylpentylthio)-2-cyclopentenone.

Fuente