Reacción #44141

Ecuación de reacción

2-(methoxy)-1-[(E)-2-(methoxy)ethenyl]-3-nitrobenzene

2-(methyloxy)-1-[(Z)-2-(methyloxy)ethenyl]-3-nitrobenzene

2-(methoxy)-3-nitrobenzaldehyde

18-Crown-6

(methoxymethyl)triphenylphosphonium chloride

potassium carbonate

sodium carbonate

→

title compound

Rendimiento 54.0%

[2-(Methoxy)-3-nitrophenyl]acetaldehyde

Rendimiento 54.0%

Disolventes

hydrochloric acid

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathen cooled to room temperature
2. 2
   Filtraciónfiltered
3. 3
   ConcentraciónThe filtrate was concentrated under vacuum
4. 4
   Otropurified by chromatography on a silica cartridge (eluent cyclohexane-ethyl acetate, 9:1)
5. 5
   Otroto give
6. 6
   Extracciónextracted with DCM
7. 7
   LavadoThe organic layer was washed (water, brine)
8. 8
   Secadodried (sodium sulfate)
9. 9
   Concentraciónconcentrated under vacuum

Procedimiento

To a stirred solution of 2-(methoxy)-3-nitrobenzaldehyde in THF were added 18-Crown-6 (0.2 eq), (methoxymethyl)triphenylphosphonium chloride (2 eq) and potassium carbonate (6.5 eq). The resulting suspension was warmed to 60° C. for 2 hours then cooled to room temperature and filtered. The filtrate was concentrated under vacuum and purified by chromatography on a silica cartridge (eluent cyclohexane-ethyl acetate, 9:1) to give a mixture of 2-(methoxy)-1-[(E)-2-(methoxy)ethenyl]-3-nitrobenzene and 2-(methyloxy)-1-[(Z)-2-(methyloxy)ethenyl]-3-nitrobenzene. The alkene mixture was dissolved in THF and 6N hydrochloric acid (1:1), and stirred for 1 hour. The solution was made basic with aqueous sodium carbonate solution and extracted with DCM. The organic layer was washed (water, brine), dried (sodium sulfate) and concentrated under vacuum to give the title compound (54% overall yield).

Fuente