Reacción #1772014

Ecuación de reacción

racemic cyclopentylmandelic acid

potassium carbonate

methyl iodide

water

→

product 2

Rendimiento 64.0%

Methyl Cyclopentylmandelate

Rendimiento 64.0%

Disolventes

methylene chloride

—

hexanes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with hexanes three times
2. 2
   OtroEvaporation of the dried hexanes
3. 3
   Extracciónextract
4. 4
   Otrogave a crude product

Procedimiento

To a mixture of racemic cyclopentylmandelic acid R/S(±)1 (4.47 g, 20 mmol) and potassium carbonate (7.01 g, 50 mmol) in DMF (50 ml), methyl iodide (8.64 g, 60 mmol) was added at room temperature. The mixture was stirred at room temperature for 2 h, and then poured into water and extracted with hexanes three times. Evaporation of the dried hexanes extract gave a crude product. Flash chromatography of the crude product on silica gel with 1.5:1 hexanes:methylene chloride gave the pure product 2 (3.02 g, 64%). 1H NMR (CDCl3, 300 MHz): 1.32-1.37, 1.43-1.69 [8H, m, (CH2)4], 2.90 [1H, p, CHC(OH)], 3.74 (1H, s, OH), 3.77 (3H, s, CH3), 7.25-7.37, 7.63-7.65 (5H, m, Ph) ppm.

Fuente