Реакция #48667

Уравнение реакции

3-tert-butyl-2,2-dichlorocyclobutanone

→

desired compound

Выход 56.0%

3-tert-butylcyclobutanone

Выход 56.0%

Растворители

Условия реакции

Обработка

1. 1
   КонцентрированиеSaturate dry methanol
2. 2
   workup.STIRRINGStir for 5 hours
3. 3
   Фильтрацияfilter
4. 4
   Концентрированиеconcentrate
5. 5
   ДругоеPartition the residue between diethyl ether and water
6. 6
   Промывкаwash the diethyl ether layer with water (twice), saturated aqueous sodium chloride solution
7. 7
   Сушкаdry (magnesium sulfate)
8. 8
   Фильтрацияfilter
9. 9
   Концентрированиеconcentrate
10. 10
    Другоеpurify
11. 11
    Промывка(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

Методика

Saturate dry methanol by stirring with excess ammonium chloride under nitrogen for 1.5 h. Add this saturated solution (150 mL) to 3-tert-butyl-2,2-dichlorocyclobutanone (7.5 g, 38.4 mmol) under nitrogen. To the resulting suspension add freshly activated zinc (15.4 g, 236 mmol). Stir for 5 hours, filter and concentrate. Partition the residue between diethyl ether and water. Discard the aqueous phase and wash the diethyl ether layer with water (twice), saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the desired compound as a clear liquid (2.71 g, 56%).

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