반응 #3100

반응 방정식

2,3-dihydrofuran

acetyl chloride

→

title compound

수율 186.7%

5-Acetyl-2,3-dihydrobenzofuran

수율 186.7%

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   온도maintaining the temperature below 5° C
2. 2
   온도while 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
   기타the layers were separated
6. 6
   세척The organic layer was washed with water and aqueous sodium bicarbonate
7. 7
   건조dried over magnesium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The residue was purified by flash chromatography on 150 g silica gel
11. 11
    세척eluting with 18% ethyl acetate in hexanes
12. 12
    기타The solvents were removed under reduced pressure

실험 절차

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.

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