反応 #48666

反応方程式

trichloroacetyl chloride

3,3-dimethyl-1-butene

ethylene glycol dimethyl ether

→

desired compound

3-tert-butyl-2,2-dichlorocyclobutanone

溶媒

diethyl ether

diethyl ether

反応条件

後処理

1. 1
   温度Heat
2. 2
   温度to reflux for 24 hours
3. 3
   ろ過filter off the residual solid materials
4. 4
   濃縮Concentrate the filtrate
5. 5
   その他triturate the residue with hexanes
6. 6
   ろ過Filter the mixture
7. 7
   その他to remove solid materials
8. 8
   洗浄Wash the filtrate solution with saturated aqueous sodium bicarbonate solution (3×), saturated aqueous sodium chloride solution
9. 9
   乾燥dry (magnesium sulfate)
10. 10
    ろ過filter
11. 11
    濃縮concentrate
12. 12
    その他purify
13. 13
    洗浄(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)
14. 14
    その他to give the pure fractions
15. 15
    濃縮concentrate

実験手順

Suspend 3,3-dimethyl-1-butene (10 mL, 80.8 mmol), ethylene glycol dimethyl ether (11.5 mL, 106 mmol), and freshly activated zinc (13.8 g, 211 mmol) in dry diethyl ether (100 mL) under a nitrogen atmosphere. Add to this suspension a solution of trichloroacetyl chloride (11.5 mL, 103 mmol) in dry diethyl ether (50 mL) dropwise over 20 minutes. Heat to reflux for 24 hours. Cool to room temperature and filter off the residual solid materials. Concentrate the filtrate and triturate the residue with hexanes. Filter the mixture to remove solid materials. Wash the filtrate solution with saturated aqueous sodium bicarbonate solution (3×), 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 pure fractions and concentrate. Isolate the desired compound by vacuum distillation to give a clear liquid (7.59 g, 48%).

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