反応 #3100

反応方程式

2,3-dihydrofuran

acetyl chloride

→

title compound

収率 186.7%

5-Acetyl-2,3-dihydrobenzofuran

収率 186.7%

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   温度maintaining the temperature below 5° C
2. 2
   温度while 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
   その他the layers were separated
6. 6
   洗浄The organic layer was washed with water and aqueous sodium bicarbonate
7. 7
   乾燥dried over magnesium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他The residue was purified by flash chromatography on 150 g silica gel
11. 11
    洗浄eluting with 18% ethyl acetate in hexanes
12. 12
    その他The solvents were removed under reduced pressure

実験手順

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.

出典