반응 #48666

반응 방정식

trichloroacetyl chloride

3,3-dimethyl-1-butene

ethylene glycol dimethyl ether

→

desired compound

3-tert-butyl-2,2-dichlorocyclobutanone

용매

diethyl ether

diethyl ether

반응 조건

후처리

1. 1
   온도Heat
2. 2
   온도to reflux for 24 hours
3. 3
   여과filter off the residual solid materials
4. 4
   농축Concentrate the filtrate
5. 5
   기타triturate the residue with hexanes
6. 6
   여과Filter the mixture
7. 7
   기타to remove solid materials
8. 8
   세척Wash the filtrate solution with saturated aqueous sodium bicarbonate solution (3×), saturated aqueous sodium chloride solution
9. 9
   건조dry (magnesium sulfate)
10. 10
    여과filter
11. 11
    농축concentrate
12. 12
    기타purify
13. 13
    세척(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)
14. 14
    기타to give the pure fractions
15. 15
    농축concentrate

실험 절차

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%).

출처