Reacción #82413

Ecuación de reacción

5,6-dimethoxy-3-phenyl-1,2,3,4-tetrahydronaphthalen-1-one

ethyl bromoacetate

lithium bis(trimethylsilyl)amide

→

title compound

Rendimiento 83.0%

2-(Carboethoxy)methyl-5,6-dimethoxy-3-phenyl-1,2,3,4-tetrahydronaph-thalen-1-one

Rendimiento 83.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched by the addition of 50 mL of saturated ammonium chloride solution
2. 2
   OtroThe resultant light yellow colored THF layer was separated
3. 3
   Otroevaporated to an oil
4. 4
   Lavadothe methylene chloride solution was washed with 2×50 mL of water and 50 mL of brine
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe residue was chromatographed on silica gel
9. 9
   Lavadoeluted with ethyl acetate/hexane (1:6)

Procedimiento

To a solution of 5,6-dimethoxy-3-phenyl-1,2,3,4-tetrahydronaphthalen-1-one (5 g, 17.7 mmol, 1.0 equivalents), the product of Example 1, in 150 mL of dry THF cooled to -78° C., was added 19.5 mL of lithium bis(trimethylsilyl)amide (1M solution in THF, 19.5 mmol, 1.1 equivalent). The resultant solution was stirred at -78° C. for 1 h and then ethyl bromoacetate (2.2 mL, 19.5 mmol, 1.1 equivalent) was added in one portion. The reaction solution was then allowed to warm to ambient temperature and was stirred for 3 h. The reaction was quenched by the addition of 50 mL of saturated ammonium chloride solution. The resultant light yellow colored THF layer was separated and evaporated to an oil. The oil was taken up into 200 mL of methylene chloride and the methylene chloride solution was washed with 2×50 mL of water and 50 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluted with ethyl acetate/hexane (1:6) to give 5.4 g (83% yield) of the title compound as a white solid; 1H NMR (CDCl3) δ: 1.2 (t, 3H, J=7.5 Hz), 2.45 (m, 2H), 3.03 (m, 1H), 3.30 (m, 2H), 3.43 (m, 1H), 3.78 (s, 3H), 3.93 (s, 3H), 4.07 (m, 2H), 6.92 (d, 1H, J=9.0 Hz), 7.32 (m, 5H), 7.89 (d, 1H, J=9.0 Hz). Analysis calculated for C22H24O5 : C, 71.72; H, 6.57. Found: C, 71.39; H, 6.63.

Fuente