Reacción #74294

Ecuación de reacción

HCl

5-methoxy-1-indanone

methyl bromobutyrate

HCl

→

product

Rendimiento 104.4%

methyl 2-(6-methoxy-1H-inden-3-yl)butanoate

Rendimiento 104.4%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   SecadoAn oven dried 5-L four-necked round-bottomed flask
2. 2
   Otrowas fitted with a thermometer, a condenser, an addition funnel, and a mechanical stirrer
3. 3
   workup.ADDITIONAfter completion of the addition
4. 4
   workup.STIRRINGthe reaction mixture was stirred at 60° C. (internal temperature) for 1 hour
5. 5
   Temperaturait was cooled in an ice-water bath
6. 6
   Otrowas kept below 20° C
7. 7
   ExtracciónThe mixture was then extracted with 1 L EtOAc
8. 8
   LavadoThe organic layer was washed with water until pH 6.0-7.0
9. 9
   Secadosaturated NaCl solution, and dried over Na2SO4

Procedimiento

An oven dried 5-L four-necked round-bottomed flask was fitted with a thermometer, a condenser, an addition funnel, and a mechanical stirrer. Under Ar protection, a suspension of 5-methoxy-1-indanone (80.0 g, 494 mmol), Zn powder (Lancaster, 56.2 g, 865 mmol) in 2 L anhydrous THF was stirred at 60° C. (internal temperature), while a solution of methyl bromobutyrate (134.1 g, 741 mmol) in 400 mL anhydrous THF was added slowly through an addition funnel. After completion of the addition, the reaction mixture was stirred at 60° C. (internal temperature) for 1 hour. The reaction was followed by TLC analysis of aliquots following 1N aqueous HCl work-up. After the reaction was completed, it was cooled in an ice-water bath followed by slow addition of 3 L of 1N HCl solution. The pot temperature was kept below 20° C. The mixture was then extracted with 1 L EtOAc. The organic layer was washed with water until pH 6.0-7.0, then saturated NaCl solution, and dried over Na2SO4. The product (127 g, >99%), a yellow oil, was obtained after solvent removal and drying under vacuum. 1H NMR (DMSO-d6) δ 7.28 (d, 1H), 7.05 (d, 1H), 6.82 (dd, 1H), 6.22 (s, 1H), 3.72 (s, 3H), 3.60 (m, 1H), 3.58 (s, 3H), 3.28 (s, 2H), 1.95 (m, 1H), 1.80 (m, 1H), 0.88 (t, 3H).

Fuente