Reacción #1885042

Ecuación de reacción

(R)-3-hydroxydihydrofuran-2(3H)-one

imidazole

t-butyldiphenylsilyl chloride

→

(R)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-one

Rendimiento 93.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was partitioned between CH2Cl2 (700 mL) and H2O (100 mL)
2. 2
   ConcentraciónThe organic portion was concentrated to dryness under reduced pressure
3. 3
   OtroThe residue was purified by silica gel chromatography (50% EtOAc in hexane)

Procedimiento

To a stirred solution of (R)-3-hydroxydihydrofuran-2(3H)-one (41.0 g, 401 mmol), imidazole (61.4 g, 920 mmol), and CH2Cl2 (175 mL) at 0° C., under N2, was added t-butyldiphenylsilyl chloride (129 mL, 138 g, 497 mmol) dropwise over 30 minutes. The mixture was stirred at room temperature for 19 hours. The mixture was partitioned between CH2Cl2 (700 mL) and H2O (100 mL). The organic portion was concentrated to dryness under reduced pressure. The residue was purified by silica gel chromatography (50% EtOAc in hexane) to afford (R)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-one (127 g, 373 mmol, 93% yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ 7.84-7.82 (m, 2H), 7.73-7.71 (m, 2H), 7.50-7.40 (m, 6H), 4.41-4.31 (m, 2H), 4.06-4.00 (m, 1H), 2.29-2.19 (m, 2H), 1.10 (s, 9H).

Fuente