反応 #44482

反応方程式

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

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他O3 was bubbled for twenty-five minutes
2. 2
   workup.ADDITIONwas added
3. 3
   その他The solvent was evaporated in vacuo
4. 4
   その他the product purified by flash column chromatography (hexanes:ethyl acetate) 100:0 to 50:50)

実験手順

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.

出典