Реакция #83190

Уравнение реакции

water

sodium hydride

tetraisopropyl methylenebisphosphonate

(E,E)-farnesyl bromide

→

Tetraisopropyl (E,E)-farnesylmethylenebisphosphonate

Выход 60.9%

Растворители

dimethoxyethane

dimethoxyethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 1 hour
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   ПромывкаThe organic layer was washed with water
4. 4
   Сушкаdried (MgSO4)
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Методика

Oily sodium hydride (60%, 0.24 g) was added to a solution of tetraisopropyl methylenebisphosphonate (3.44 g) in dimethoxyethane (25 ml). The mixture was stirred at room temperature for 1 hour. Then, a solution of (E,E)-farnesyl bromide (1.43 g) in dimethoxyethane (5 ml) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 hour, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), and then the solvent was distilled off under reduced pressure. The oily residue was subjected to column chromatography on silica gel. Tetraisopropyl (E,E)-farnesylmethylenebisphosphonate (1.67 g, 60.9%) was obtained as an oil from the fractions obtained by elution with ethyl acetate-chloroform (1:1, v/v).

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