Reacción #44482

Ecuación de reacción

N2

DMS

solution

3-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-pent-4-enoic acid methyl ester

methanol

→

title compound

3-(tert-butyl-dimethyl-silanoxymethyl)-2,2-dimethyl-4-oxo-butyric acid methyl ester

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroO3 was bubbled for twenty-five minutes
2. 2
   workup.ADDITIONwas added
3. 3
   OtroThe solvent was evaporated in vacuo
4. 4
   Otrothe product purified by flash column chromatography (hexanes:ethyl acetate) 100:0 to 50:50)

Procedimiento

A solution of Example 2C (3.5 g, 12.2 mmol)in dichloromethane (25 mL) and methanol (2.5 mL) was cooled to −78° C. and O3 was bubbled for twenty-five minutes. The reaction was purged with N2 and DMS (5.29 g, 85.4 mmol) was added. The reaction was stirred at room temperature for three hours. The solvent was evaporated in vacuo and the product purified by flash column chromatography (hexanes:ethyl acetate) 100:0 to 50:50) to provide the title compound as an oil.

Fuente