Реакция #44482

Уравнение реакции

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

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеO3 was bubbled for twenty-five minutes
2. 2
   workup.ADDITIONwas added
3. 3
   ДругоеThe solvent was evaporated in vacuo
4. 4
   Другоеthe product purified by flash column chromatography (hexanes:ethyl acetate) 100:0 to 50:50)

Методика

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.

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