Реакция #330931

Уравнение реакции

ammonium chloride

methyl (4-oxo-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-yl)acetate

bromocyclopropane

magnesium

→

captioned compound

Выход 79.0%

Methyl (4-Cyclopropyl-4-hydroxy-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-yl)acetate

Выход 79.0%

Растворители

THF

THF

THF

Условия реакции

Обработка

1. 1
   Температураwhile heating
2. 2
   workup.ADDITIONAfter the termination of dropwise addition
3. 3
   Температураthe mixture was refluxed
4. 4
   Температураunder heating for an additional 2 hours
5. 5
   Температураto air-cool
6. 6
   Температураpreviously chilled in an ice bath
7. 7
   Экстракцияthe mixture was extracted with ethyl acetate
8. 8
   ПромывкаThe organic layer was washed with an aqueous saturated sodium chloride solution
9. 9
   Сушкаdried over anhydrous sodium sulfate
10. 10
    workup.DISTILLATIONThe solvents were distilled off under a reduced pressure
11. 11
    Другоеthe residue obtained
12. 12
    Другоеwas purified by silica gel column chromatography (hexane-ethyl acetate=5:1)

Методика

An anhydrous THF (50 mL) solution of bromocyclopropane (8.3 mL) was added dropwise to a metal magnesium (2.5 g), while heating. After the termination of dropwise addition, an anhydrous THF (20 mL) was added thereto, and the mixture was refluxed under heating for an additional 2 hours. Thereafter, the reaction mixture was allowed to air-cool, and this solution was added dropwise to an anhydrous THF (30 mL) solution of methyl (4-oxo-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-yl)acetate (10.0 g) previously chilled in an ice bath. After stirring the mixture for 30 minutes, an aqueous saturated ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and thereafter dried over anhydrous sodium sulfate. The solvents were distilled off under a reduced pressure, and the residue obtained was purified by silica gel column chromatography (hexane-ethyl acetate=5:1), to give 9.0 g (79%) of the captioned compound as an oily product.

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