Реакция #3100

Уравнение реакции

2,3-dihydrofuran

acetyl chloride

→

title compound

Выход 186.7%

5-Acetyl-2,3-dihydrobenzofuran

Выход 186.7%

Растворители

methylene chloride

methylene chloride

Условия реакции

Обработка

1. 1
   Температураmaintaining the temperature below 5° C
2. 2
   Температураwhile 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
   Другоеthe layers were separated
6. 6
   ПромывкаThe organic layer was washed with water and aqueous sodium bicarbonate
7. 7
   Сушкаdried over magnesium sulfate
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    ДругоеThe residue was purified by flash chromatography on 150 g silica gel
11. 11
    Промывкаeluting with 18% ethyl acetate in hexanes
12. 12
    ДругоеThe solvents were removed under reduced pressure

Методика

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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