Reaktion #3100

Reaktionsgleichung

2,3-dihydrofuran

acetyl chloride

→

title compound

Ausbeute 186.7%

5-Acetyl-2,3-dihydrobenzofuran

Ausbeute 186.7%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintaining the temperature below 5° C
2. 2
   Temperaturwhile 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
   Sonstigethe layers were separated
6. 6
   WaschenThe organic layer was washed with water and aqueous sodium bicarbonate
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe residue was purified by flash chromatography on 150 g silica gel
11. 11
    Wascheneluting with 18% ethyl acetate in hexanes
12. 12
    SonstigeThe solvents were removed under reduced pressure

Vorschrift

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.

Quelle