Реакция #1346181

Уравнение реакции

water

α-hydroxybutyrolactone

linoleyl methane sulfonate

cesium carbonate

→

3-((9Z,12Z)-octadeca-9,12-dienyloxy)dihydrofuran-2(3H)-one

Выход 63.6%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate (3×100 mL)
2. 2
   ПромывкаThe combined ethyl acetate extracts were washed with brine (3×50 mL)
3. 3
   Другоеdried on magnesium sulfate
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo to dryness
6. 6
   ДругоеThe residue was purified by column chromatography on silica gel 60 (eluted with 10% ethyl acetate in hexanes)

Методика

To a solution of α-hydroxybutyrolactone (2.0 g, 19.6 mmol) and linoleyl methane sulfonate (5.4 g, 15.7 mmol) in anhydrous DMF (60 mL), was added cesium carbonate (8.0 g, 24.5 mmol). The solution was stirred overnight under nitrogen at 80° C. Upon completion, the reaction was poured into water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined ethyl acetate extracts were washed with brine (3×50 mL), dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (eluted with 10% ethyl acetate in hexanes) to afford 3-((9Z,12Z)-octadeca-9,12-dienyloxy)dihydrofuran-2(3H)-one as a pale yellow oil (3.5 g, 51%).

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