Реакция #1666

Уравнение реакции

dimethylcarbonate

sodium hydride

5-chloroindanone

hydrogen

→

desired product

Выход 45.0%

2 -carbomethoxy-5-chloroindanone

Выход 45.0%

Растворители

dimethoxyethane

dimethoxyethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added dropwise at room temperature
2. 2
   ТемператураThe reaction was cooled to room temperature
3. 3
   Другоеquenched with 100 ml H2O
4. 4
   Экстракцияextracted with ethyl ether (3×100 ml)
5. 5
   ЭкстракцияThe ether extract
6. 6
   Промывкаwas washed with brine (100 ml)
7. 7
   Сушкаdried over anhydrous MgSO4

Методика

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.

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