Reacción #3494

Ecuación de reacción

1-Indanone

butyl lithium

ethyl chloroformate

→

2-carbethoxy-1-indanone

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with nitrogen inlet
2. 2
   workup.WAITslowly brought to room temperature in about one hour
3. 3
   Otroby evaporating the THF
4. 4
   Otrothe product was chromatographed

Procedimiento

1-Indanone (1.5 g, 11.36 mmols) was dissolved in dry THF in a three neck flask equipped with nitrogen inlet, septum and a guard tube. The flask was cooled to -20° C. for 10 minutes. Then butyl lithium (11.37 ml, 12.48 mmols) was added dropwise through the septum using the syringe. The reaction mixture was allowed to stand at -20° C. for 45 minutes and then ethyl chloroformate (1.08 ml, 10 mmols) was added dropwise using a syringe. The reaction mixture was stirred at -20° C. for 30 minutes and slowly brought to room temperature in about one hour. The reaction was worked-up by evaporating the THF and the product was chromatographed to yield 2-carbethoxy-1-indanone. NMR: (CDCl3):δ:1.25 (t, 3H, OCH2CH3); 3.45 (d, 2H, benzylic CH2); 3.65 (t, 1H, COCHCO); 4.2 (q, 2H, OCH2CH3); 7.4-7.5 (m, 4H, Ar-H).

Fuente