Реакция #1256725

Уравнение реакции

methyl 5-propyl-2-trifluoromethanesulfonyloxycyclohex-1-enecarboxylate

4-ethoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzeneboronic acid

sodium metaborate

hydrazinium hydroxide

→

3-ethoxy-4-fluoro-8-propyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

Растворители

water

water

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеthe aqueous phase is separated off
2. 2
   Экстракцияextracted twice with MTB ether
3. 3
   ПромывкаThe combined organic phases are washed with saturated sodium chloride soln
4. 4
   Сушкаand dried over sodium sulfate
5. 5
   ДругоеThe solvent is removed under reduced pressure
6. 6
   Фильтрацияthe residue is filtered through silica gel with n-heptane/MTB ether (6:4)

Методика

18.2 g (56.6 mmol) of methyl 5-propyl-2-trifluoromethanesulfonyloxycyclohex-1-enecarboxylate, 21.5 g (74.6 mmol) of 4-ethoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzeneboronic acid, 1.5 ml of water, 33 g (120 mmol) of sodium metaborate, 1.12 g (1.6 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.1 ml (1.6 mmol) of hydrazinium hydroxide are heated under reflux overnight in 300 ml of tetrahydrofuran. After addition of water, the aqueous phase is separated off and extracted twice with MTB ether. The combined organic phases are washed with saturated sodium chloride soln. and dried over sodium sulfate. The solvent is removed under reduced pressure, and the residue is filtered through silica gel with n-heptane/MTB ether (6:4), giving 3-ethoxy-4-fluoro-8-propyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one as colourless crystals.

Источник