Reaction #44482

Reaction equation

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

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherO3 was bubbled for twenty-five minutes
2. 2
   workup.ADDITIONwas added
3. 3
   OtherThe solvent was evaporated in vacuo
4. 4
   Otherthe product purified by flash column chromatography (hexanes:ethyl acetate) 100:0 to 50:50)

Procedure

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.

Source