Реакция #990806

Уравнение реакции

sodium ethoxide

sodium

bromoacetaldehyde diethylacetal

3-acetylmercaptocycloheptene

→

3-[(2,2-diethoxyethyl)thio]-1-cycloheptene

Выход 99.4%

Растворители

ethanol

ethanol

ethanol

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was heated
2. 2
   Температураunder reflux for 15 minutes
3. 3
   ТемператураThe reaction mixture was heated
4. 4
   Температураunder reflux for 2.0 hours
5. 5
   Температураcooled
6. 6
   ФильтрацияThe precipitated sodium bromide was filtered
7. 7
   Промывкаwashed well with absolute ethanol
8. 8
   КонцентрированиеThe filtrate was concentrated
9. 9
   Другоеthe residue partitioned between ether/brine
10. 10
    ЭкстракцияThe aqueous phase was further extracted with ether
11. 11
    Сушкаdried over magnesium sulfate
12. 12
    Другоеevaporated

Методика

A solution of fresh sodium ethoxide prepared from 7.6 g (0.330 gram-atom metallic sodium) in 200 ml of absolute ethanol was treated dropwise with 56.18 g (0.330 mole) of 3-acetylmercaptocycloheptene in 10 ml of absolute ethanol. The reaction was heated under reflux for 15 minutes and then cooled to room temperature. A solution of 49.69 ml (0.330 mole) of bromoacetaldehyde diethylacetal in 30 ml of absolute ethanol was added dropwise. The reaction mixture was heated under reflux for 2.0 hours and cooled. The precipitated sodium bromide was filtered and washed well with absolute ethanol. The filtrate was concentrated and the residue partitioned between ether/brine. The aqueous phase was further extracted with ether. The organic extracts were pooled, dried over magnesium sulfate, and evaporated to afford 80.1 g (0.328 mole, 99%) of pure 3-[(2,2-diethoxyethyl)thio]-1-cycloheptene, as a colorless oil.

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