تفاعل #3100

معادلة التفاعل

2,3-dihydrofuran

acetyl chloride

→

title compound

المردود 186.7%

5-Acetyl-2,3-dihydrobenzofuran

المردود 186.7%

المذيبات

methylene chloride

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةmaintaining the temperature below 5° C
2. 2
   درجة الحرارةwhile 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
   أخرىthe layers were separated
6. 6
   غسيلThe organic layer was washed with water and aqueous sodium bicarbonate
7. 7
   تجفيفdried over magnesium sulfate
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated under reduced pressure
10. 10
    أخرىThe residue was purified by flash chromatography on 150 g silica gel
11. 11
    غسيلeluting with 18% ethyl acetate in hexanes
12. 12
    أخرىThe solvents were removed under reduced pressure

الإجراء التجريبي

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.

المصدر