Reacción #1256725

Ecuación de reacción

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

Disolventes

water

water

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe aqueous phase is separated off
2. 2
   Extracciónextracted twice with MTB ether
3. 3
   LavadoThe combined organic phases are washed with saturated sodium chloride soln
4. 4
   Secadoand dried over sodium sulfate
5. 5
   OtroThe solvent is removed under reduced pressure
6. 6
   Filtraciónthe residue is filtered through silica gel with n-heptane/MTB ether (6:4)

Procedimiento

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.

Fuente