반응 #1666

반응 방정식

dimethylcarbonate

sodium hydride

5-chloroindanone

hydrogen

→

desired product

수율 45.0%

2 -carbomethoxy-5-chloroindanone

수율 45.0%

용매

dimethoxyethane

dimethoxyethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise at room temperature
2. 2
   온도The reaction was cooled to room temperature
3. 3
   기타quenched with 100 ml H2O
4. 4
   추출extracted with ethyl ether (3×100 ml)
5. 5
   추출The ether extract
6. 6
   세척was washed with brine (100 ml)
7. 7
   건조dried over anhydrous MgSO4

실험 절차

To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) was added dropwise at room temperature and the reaction was heated to 60° C. for one hour. The reaction was cooled to room temperature, quenched with 100 ml H2O, acidified to pH 5 with concentrated HCl and extracted with ethyl ether (3×100 ml). The ether extract was washed with brine (100 ml), dried over anhydrous MgSO4 and stripped to yield 3.0 g (45%) of the desired product as a tan solid.

출처