Reacción #219871

Ecuación de reacción

4-methyl-1-cyanonaphthalene

LDA

methyl chloroformate

→

(4-Cyanonaphthalen-1-yl)acetic acid methyl ester

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamaintained at 0° C. for 30 min
2. 2
   TemperaturaThe resulting red-colored solution was cooled to −78° C.
3. 3
   Temperaturawhile warming to rt until the displacement
4. 4
   Otro(4 h)
5. 5
   Otroquenched with sat'd NH4Cl
6. 6
   OtroThe THF layer was evaporated
7. 7
   Extracciónextracted with EtOAc (3×20 mL)
8. 8
   SecadoThe EtOAc was dried over Na2SO4
9. 9
   Concentraciónconcentrated in vacuo
10. 10
    Otroto afford an oil

Procedimiento

To a solution of 4-methyl-1-cyanonaphthalene (4.35 g, 25.9 mmol) in THF (100 mL) was cooled to −78° C. and treated with commercially available LDA (2 M, 60 mL). The reaction mixture was then warmed to 0° C. and maintained at 0° C. for 30 min. The resulting red-colored solution was cooled to −78° C. and methyl chloroformate (10 mL, 130 mmol) was added. The reaction mixture was stirred while warming to rt until the displacement was complete (4 h) and then quenched with sat'd NH4Cl. The THF layer was evaporated and extracted with EtOAc (3×20 mL). The EtOAc was dried over Na2SO4 and concentrated in vacuo to afford an oil.

Fuente