Реакция #55935

Уравнение реакции

water

1-(m-methoxyphenyl)-7-(5-methyl-2-furyl)-3-heptyn-5-ol

water

sulphuric acid

→

3-methyl-2-[6-(m-methoxyphenyl)-2-hydroxy-3-hexynyl]-2-cyclopentenone

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling
2. 2
   Экстракцияextracted with methylene chloride
3. 3
   ПромывкаThe methylene chloride layer was washed with water
4. 4
   Другоеevaporated to dryness under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue (10.60 g) was dissolved in 500 ml of about 0.1 N ethanolic potassium hydroxide solution
6. 6
   ТемператураAfter cooling
7. 7
   workup.ADDITIONthe mixture was poured into 1000 ml water
8. 8
   Экстракцияextracted with methylene chloride
9. 9
   ПромывкаThe methylene chloride layer was washed with water
10. 10
    Другоеevaporated to dryness under reduced pressure

Методика

A solution of 10.00 g (33.6 mmol) dl-1-(m-methoxyphenyl)-7-(5-methyl-2-furyl)-3-heptyn-5-ol in 20 ml acetic acid, about 10 ml water and 0.40 ml about 20% sulphuric acid was stirred under nitrogen in an oil-bath at 90° C. for about 24 hours. After cooling, the mixture was poured into 200 ml water and extracted with methylene chloride. The methylene chloride layer was washed with water and evaporated to dryness under reduced pressure. The residue (10.60 g) was dissolved in 500 ml of about 0.1 N ethanolic potassium hydroxide solution and stirred under nitrogen in an oil-bath at about 80° C. for about 1 hour. After cooling, the mixture was poured into 1000 ml water and extracted with methylene chloride. The methylene chloride layer was washed with water and evaporated to dryness under reduced pressure. Yield: 9.85 g.

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