Reacción #1666

Ecuación de reacción

dimethylcarbonate

sodium hydride

5-chloroindanone

hydrogen

→

desired product

Rendimiento 45.0%

2 -carbomethoxy-5-chloroindanone

Rendimiento 45.0%

Disolventes

dimethoxyethane

dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise at room temperature
2. 2
   TemperaturaThe reaction was cooled to room temperature
3. 3
   Otroquenched with 100 ml H2O
4. 4
   Extracciónextracted with ethyl ether (3×100 ml)
5. 5
   ExtracciónThe ether extract
6. 6
   Lavadowas washed with brine (100 ml)
7. 7
   Secadodried over anhydrous MgSO4

Procedimiento

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.

Fuente