Reacción #3100

Ecuación de reacción

2,3-dihydrofuran

acetyl chloride

→

title compound

Rendimiento 186.7%

5-Acetyl-2,3-dihydrobenzofuran

Rendimiento 186.7%

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamaintaining the temperature below 5° C
2. 2
   Temperaturawhile maintaining the temperature below 8° C
3. 3
   workup.STIRRINGThe dark red solution was stirred 1 hour at 2° C.
4. 4
   workup.STIRRINGThe reaction was stirred an additional 30 minutes
5. 5
   Otrothe layers were separated
6. 6
   LavadoThe organic layer was washed with water and aqueous sodium bicarbonate
7. 7
   Secadodried over magnesium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    OtroThe residue was purified by flash chromatography on 150 g silica gel
11. 11
    Lavadoeluting with 18% ethyl acetate in hexanes
12. 12
    OtroThe solvents were removed under reduced pressure

Procedimiento

To a 0° C. solution of acetyl chloride (1.64 mL, 23.0 mmol, 1.3 equivalents) in methylene chloride (30 mL) was added stannic chloride (2.49 mL, 21.3 mmol, 1.2 equivalents), maintaining the temperature below 5° C. The solution was stirred 15 minutes at 0° C., and then a solution of 2,3-dihydrofuran (2.00 mL, 17.7 mmol) in methylene chloride (5 mL) was added dropwise while maintaining the temperature below 8° C. The dark red solution was stirred 1 hour at 2° C. and then poured into 50 mL of ice water. The reaction was stirred an additional 30 minutes, and the layers were separated. The organic layer was washed with water and aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on 150 g silica gel, eluting with 18% ethyl acetate in hexanes. The solvents were removed under reduced pressure to yield the title compound (2.68 g, 93%) as a yellow solid.

Fuente