Реакция #1153709

Уравнение реакции

hydrochloric acid

sodium hydride

ethyl 4-chlorophenylacetate

ethyl formate

→

ethyl 2-(4′-chlorophenyl)-2-formylacetate

Выход 78.4%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added dropwise at 5° to 10° C
2. 2
   workup.STIRRINGthe mixture was further stirred at room temperature for 4.5 hours
3. 3
   ДругоеAfter completion of the reaction
4. 4
   Температураthe reaction mixture was cooled to ice temperature
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe residue was subjected to phase separation with ethyl acetatewater
7. 7
   Другоеthe organic layer was dried
8. 8
   Концентрированиеconcentrated

Методика

Then, 4.19 g of sodium hydride (60% in oil) was suspended in 150 ml of tetrahydrofuran, to which a solution of 19.0 g of ethyl 4-chlorophenylacetate in 150 ml of tetrahydrofuran was added dropwise at 5° to 10° C. After stirring at room temperature for 1.5 hours, 8.42 g of ethyl formate was added, and the mixture was further stirred at room temperature for 4.5 hours. After completion of the reaction, the reaction mixture was cooled to ice temperature, neutralized by the addition of diluted hydrochloric acid, and concentrated. The residue was subjected to phase separation with ethyl acetatewater, and the organic layer was dried and then concentrated. The residue was subjected to silica gel chromatography, which afforded 17.0 g of ethyl 2-(4′-chlorophenyl)-2-formylacetate.

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