Реакция #216249

Уравнение реакции

stearoyl chloride

Meldrum's acid

pyridine

→

methyl 3-oxoeicosanoate

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Промывкаwas washed with 4N hydrochloric acid
2. 2
   Экстракцияthe aqueous phase was back-extracted with methylene chloride
3. 3
   Сушкаthe methylene chloride phase was dried
4. 4
   Концентрированиеconcentrated
5. 5
   workup.STIRRINGstirred
6. 6
   Температураunder reflux
7. 7
   ТемператураAfter cooling the separated crystals
8. 8
   Фильтрацияwere filtered off
9. 9
   workup.DISSOLUTIONdissolved in methylene chloride
10. 10
    Другоеchromatographed on silica gel with methylene chloride

Методика

270 ml of stearoyl chloride were added dropwise at a maximum of 150° C. to a solution of 117 g of Meldrum's acid and 131 ml of pyridine in 1.51 of methylene chloride. After stirring the reaction mixture was washed with 4N hydrochloric acid, the aqueous phase was back-extracted with methylene chloride and the methylene chloride phase was dried and concentrated. The residue was taken up in methanol and stirred under reflux. After cooling the separated crystals were filtered off, dissolved in methylene chloride and chromatographed on silica gel with methylene chloride. There were obtained 175 g of methyl 3-oxoeicosanoate, m.p. 52°-54° C.

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