Реакция #63782

Уравнение реакции

2-Chloro-4-(methylsulfonyl)benzoyl chloride

4,4-dimethyl-5-phenyl-1,3-cyclohexanedione

Acetone cyanohydrin

triethylamine

Triethylamine

→

desired product

Выход 30.8%

2-[2-Chloro-4-(methylsulfonyl)benzoyl]-4,4-dimethyl-5-phenyl-1,3-cyclohexanedione

Выход 30.8%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 1.5 hour
2. 2
   КонцентрированиеThe reaction mixture was concentrated under vacuum
3. 3
   workup.DISSOLUTIONthe residue dissolved in 100 ml of methylene chloride
4. 4
   ПромывкаThe methylene chloride solution was washed with 2N hydrochloric acid, 10% cupric acetate, water, 5% potassium carbonate, 2N hydrochloric acid, and water
5. 5
   СушкаThe methylene chloride solution was dried over anhydrous magnesium sulate
6. 6
   Концентрированиеconcentrated under vacuum

Методика

2-Chloro-4-(methylsulfonyl)benzoyl chloride (2.3 g, 9 mmol) and 4,4-dimethyl-5-phenyl-1,3-cyclohexanedione (2.0 g, 9 mmol) were dissolved in 50 ml of acetonitrile. Triethylamine (1.8 g, 18 mmol) was added dropwise and the resulting solution was stirred at room temperature for 1 hour. Acetone cyanohydrin (0.17 g, 2 mmol) and triethylamine (1.8 g, 18 mmol) were added and the reaction mixture was stirred at room temperature for 1.5 hour. The reaction mixture was concentrated under vacuum and the residue dissolved in 100 ml of methylene chloride. The methylene chloride solution was washed with 2N hydrochloric acid, 10% cupric acetate, water, 5% potassium carbonate, 2N hydrochloric acid, and water. The methylene chloride solution was dried over anhydrous magnesium sulate and concentrated under vacuum, yielding 1.2 g of the desired product as a viscous oil. It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

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